EP1964893A1 - Composition d'encre, procédé d'enregistrement à jet d'encre, matériau imprimé et ensemble d'encres - Google Patents
Composition d'encre, procédé d'enregistrement à jet d'encre, matériau imprimé et ensemble d'encres Download PDFInfo
- Publication number
- EP1964893A1 EP1964893A1 EP20080002529 EP08002529A EP1964893A1 EP 1964893 A1 EP1964893 A1 EP 1964893A1 EP 20080002529 EP20080002529 EP 20080002529 EP 08002529 A EP08002529 A EP 08002529A EP 1964893 A1 EP1964893 A1 EP 1964893A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- parts
- ink
- ink composition
- manufactured
- pigment
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 222
- 238000000034 method Methods 0.000 title claims abstract description 51
- 239000000463 material Substances 0.000 title claims abstract description 21
- 239000000178 monomer Substances 0.000 claims abstract description 78
- 239000000049 pigment Substances 0.000 claims abstract description 71
- 230000005855 radiation Effects 0.000 claims abstract description 38
- 239000002270 dispersing agent Substances 0.000 claims abstract description 37
- 239000003505 polymerization initiator Substances 0.000 claims abstract description 30
- 238000007599 discharging Methods 0.000 claims abstract description 6
- 230000001678 irradiating effect Effects 0.000 claims abstract description 6
- 125000003118 aryl group Chemical group 0.000 claims description 29
- 239000003086 colorant Substances 0.000 claims description 27
- 238000005286 illumination Methods 0.000 claims description 6
- 239000000976 ink Substances 0.000 description 381
- 150000001875 compounds Chemical class 0.000 description 95
- -1 tetrahydrofurfuryl group Chemical group 0.000 description 84
- 239000002585 base Substances 0.000 description 81
- 238000011156 evaluation Methods 0.000 description 72
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 60
- 238000002360 preparation method Methods 0.000 description 51
- 239000002609 medium Substances 0.000 description 38
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 36
- 239000012965 benzophenone Substances 0.000 description 26
- JWYVGKFDLWWQJX-UHFFFAOYSA-N 1-ethenylazepan-2-one Chemical compound C=CN1CCCCCC1=O JWYVGKFDLWWQJX-UHFFFAOYSA-N 0.000 description 25
- 150000002148 esters Chemical class 0.000 description 25
- FNYWFRSQRHGKJT-UHFFFAOYSA-N 3-ethyl-3-[(3-ethyloxetan-3-yl)methoxymethyl]oxetane Chemical compound C1OCC1(CC)COCC1(CC)COC1 FNYWFRSQRHGKJT-UHFFFAOYSA-N 0.000 description 24
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical group C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 24
- PODOEQVNFJSWIK-UHFFFAOYSA-N diphenylphosphoryl-(2,4,6-trimethoxyphenyl)methanone Chemical compound COC1=CC(OC)=CC(OC)=C1C(=O)P(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 PODOEQVNFJSWIK-UHFFFAOYSA-N 0.000 description 24
- CYIGRWUIQAVBFG-UHFFFAOYSA-N 1,2-bis(2-ethenoxyethoxy)ethane Chemical compound C=COCCOCCOCCOC=C CYIGRWUIQAVBFG-UHFFFAOYSA-N 0.000 description 23
- JUXZNIDKDPLYBY-UHFFFAOYSA-N 3-ethyl-3-(phenoxymethyl)oxetane Chemical compound C=1C=CC=CC=1OCC1(CC)COC1 JUXZNIDKDPLYBY-UHFFFAOYSA-N 0.000 description 22
- VCFFZAQQHCLMNH-UHFFFAOYSA-N [3-(6-prop-2-enoyloxyhexanoyloxy)-2-[[3-(6-prop-2-enoyloxyhexanoyloxy)-2,2-bis(6-prop-2-enoyloxyhexanoyloxymethyl)propoxy]methyl]-2-(6-prop-2-enoyloxyhexanoyloxymethyl)propyl] 6-prop-2-enoyloxyhexanoate Chemical compound C=CC(=O)OCCCCCC(=O)OCC(COC(=O)CCCCCOC(=O)C=C)(COC(=O)CCCCCOC(=O)C=C)COCC(COC(=O)CCCCCOC(=O)C=C)(COC(=O)CCCCCOC(=O)C=C)COC(=O)CCCCCOC(=O)C=C VCFFZAQQHCLMNH-UHFFFAOYSA-N 0.000 description 22
- 239000000126 substance Substances 0.000 description 20
- QNODIIQQMGDSEF-UHFFFAOYSA-N (1-hydroxycyclohexyl)-phenylmethanone Chemical compound C=1C=CC=CC=1C(=O)C1(O)CCCCC1 QNODIIQQMGDSEF-UHFFFAOYSA-N 0.000 description 19
- 239000007787 solid Substances 0.000 description 19
- 239000011324 bead Substances 0.000 description 18
- 230000002093 peripheral effect Effects 0.000 description 18
- 238000001723 curing Methods 0.000 description 15
- 238000003860 storage Methods 0.000 description 14
- SUDBRAWXUGTELR-HPFNVAMJSA-N 5-[[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]-1h-pyrimidine-2,4-dione Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OCC1=CNC(=O)NC1=O SUDBRAWXUGTELR-HPFNVAMJSA-N 0.000 description 13
- BIDWUUDRRVHZLQ-UHFFFAOYSA-N 3-ethyl-3-(2-ethylhexoxymethyl)oxetane Chemical compound CCCCC(CC)COCC1(CC)COC1 BIDWUUDRRVHZLQ-UHFFFAOYSA-N 0.000 description 12
- 238000006116 polymerization reaction Methods 0.000 description 11
- 239000011347 resin Substances 0.000 description 11
- 229920005989 resin Polymers 0.000 description 11
- 230000035945 sensitivity Effects 0.000 description 11
- 0 C=CC(OCC*c1c(cccc2)c2ccc1)=O Chemical compound C=CC(OCC*c1c(cccc2)c2ccc1)=O 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- 239000004094 surface-active agent Substances 0.000 description 10
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 9
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 9
- 238000010538 cationic polymerization reaction Methods 0.000 description 9
- VVOLVFOSOPJKED-UHFFFAOYSA-N copper phthalocyanine Chemical compound [Cu].N=1C2=NC(C3=CC=CC=C33)=NC3=NC(C3=CC=CC=C33)=NC3=NC(C3=CC=CC=C33)=NC3=NC=1C1=CC=CC=C12 VVOLVFOSOPJKED-UHFFFAOYSA-N 0.000 description 9
- 238000012360 testing method Methods 0.000 description 9
- 239000010936 titanium Substances 0.000 description 9
- 229910052719 titanium Inorganic materials 0.000 description 9
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 8
- 230000000977 initiatory effect Effects 0.000 description 8
- 239000002245 particle Substances 0.000 description 8
- 125000000217 alkyl group Chemical group 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 7
- 239000006185 dispersion Substances 0.000 description 7
- 239000002244 precipitate Substances 0.000 description 7
- 239000007870 radical polymerization initiator Substances 0.000 description 7
- 230000001235 sensitizing effect Effects 0.000 description 7
- 239000002253 acid Substances 0.000 description 6
- 150000008365 aromatic ketones Chemical class 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- 125000004122 cyclic group Chemical group 0.000 description 6
- ZSWFCLXCOIISFI-UHFFFAOYSA-N endo-cyclopentadiene Natural products C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 6
- 239000003999 initiator Substances 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 6
- 125000001424 substituent group Chemical group 0.000 description 6
- 239000012956 1-hydroxycyclohexylphenyl-ketone Substances 0.000 description 5
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical group NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 150000007514 bases Chemical class 0.000 description 5
- 238000005452 bending Methods 0.000 description 5
- 238000010894 electron beam technology Methods 0.000 description 5
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 5
- 229910052753 mercury Inorganic materials 0.000 description 5
- 230000008569 process Effects 0.000 description 5
- 241000894007 species Species 0.000 description 5
- 229910052717 sulfur Inorganic materials 0.000 description 5
- OQCFWECOQNPQCG-UHFFFAOYSA-N 1,3,4,8-tetrahydropyrimido[4,5-c]oxazin-7-one Chemical compound C1CONC2=C1C=NC(=O)N2 OQCFWECOQNPQCG-UHFFFAOYSA-N 0.000 description 4
- 239000006096 absorbing agent Substances 0.000 description 4
- 239000003963 antioxidant agent Substances 0.000 description 4
- 230000003078 antioxidant effect Effects 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 230000008859 change Effects 0.000 description 4
- 229920001577 copolymer Polymers 0.000 description 4
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 4
- 150000002605 large molecules Chemical class 0.000 description 4
- PMJFVKWBSWWAKT-UHFFFAOYSA-N n-cyclohexylprop-2-enamide Chemical compound C=CC(=O)NC1CCCCC1 PMJFVKWBSWWAKT-UHFFFAOYSA-N 0.000 description 4
- 229940059574 pentaerithrityl Drugs 0.000 description 4
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 4
- 238000000016 photochemical curing Methods 0.000 description 4
- 229920001223 polyethylene glycol Polymers 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- WYROLENTHWJFLR-ACLDMZEESA-N queuine Chemical compound C1=2C(=O)NC(N)=NC=2NC=C1CN[C@H]1C=C[C@H](O)[C@@H]1O WYROLENTHWJFLR-ACLDMZEESA-N 0.000 description 4
- 238000011160 research Methods 0.000 description 4
- 125000004434 sulfur atom Chemical group 0.000 description 4
- 239000012463 white pigment Substances 0.000 description 4
- 239000001052 yellow pigment Substances 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 3
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 3
- 239000002202 Polyethylene glycol Substances 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 125000002015 acyclic group Chemical group 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- MQDJYUACMFCOFT-UHFFFAOYSA-N bis[2-(1-hydroxycyclohexyl)phenyl]methanone Chemical compound C=1C=CC=C(C(=O)C=2C(=CC=CC=2)C2(O)CCCCC2)C=1C1(O)CCCCC1 MQDJYUACMFCOFT-UHFFFAOYSA-N 0.000 description 3
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical class C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 3
- 150000001721 carbon Chemical group 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N coumarin Chemical compound C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 239000012954 diazonium Substances 0.000 description 3
- 239000002612 dispersion medium Substances 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- 239000011737 fluorine Substances 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 229920000139 polyethylene terephthalate Polymers 0.000 description 3
- 239000005020 polyethylene terephthalate Substances 0.000 description 3
- 229920001451 polypropylene glycol Polymers 0.000 description 3
- 238000001556 precipitation Methods 0.000 description 3
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 3
- 238000003847 radiation curing Methods 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- 238000012546 transfer Methods 0.000 description 3
- 239000012855 volatile organic compound Substances 0.000 description 3
- DTGKSKDOIYIVQL-WEDXCCLWSA-N (+)-borneol Chemical group C1C[C@@]2(C)[C@@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-WEDXCCLWSA-N 0.000 description 2
- OVDYCAUPPUEIJO-UHFFFAOYSA-N (4-tert-butylphenyl)-diphenylphosphorylmethanone Chemical compound C1=CC(C(C)(C)C)=CC=C1C(=O)P(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 OVDYCAUPPUEIJO-UHFFFAOYSA-N 0.000 description 2
- YXIWHUQXZSMYRE-UHFFFAOYSA-N 1,3-benzothiazole-2-thiol Chemical compound C1=CC=C2SC(S)=NC2=C1 YXIWHUQXZSMYRE-UHFFFAOYSA-N 0.000 description 2
- FNDZYHVAAIPVCS-UHFFFAOYSA-N 1-[methoxy(phenyl)phosphoryl]-2,2-dimethylpropan-1-one Chemical compound CC(C)(C)C(=O)P(=O)(OC)C1=CC=CC=C1 FNDZYHVAAIPVCS-UHFFFAOYSA-N 0.000 description 2
- QDJHMOSPJGJYPX-UHFFFAOYSA-N 2,2-dimethyl-1-[phenyl(propan-2-yloxy)phosphoryl]propan-1-one Chemical compound CC(C)OP(=O)(C(=O)C(C)(C)C)C1=CC=CC=C1 QDJHMOSPJGJYPX-UHFFFAOYSA-N 0.000 description 2
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- 239000004698 Polyethylene Substances 0.000 description 2
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- 239000004793 Polystyrene Substances 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
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- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- NKJRPAWZCFIXFA-UHFFFAOYSA-N [(2,5-dimethylphenyl)-(2-methylnaphthalene-1-carbonyl)phosphoryl]-(2-methylnaphthalen-1-yl)methanone Chemical compound CC1=CC=C(C)C(P(=O)(C(=O)C=2C3=CC=CC=C3C=CC=2C)C(=O)C=2C3=CC=CC=C3C=CC=2C)=C1 NKJRPAWZCFIXFA-UHFFFAOYSA-N 0.000 description 2
- GUCYFKSBFREPBC-UHFFFAOYSA-N [phenyl-(2,4,6-trimethylbenzoyl)phosphoryl]-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)P(=O)(C=1C=CC=CC=1)C(=O)C1=C(C)C=C(C)C=C1C GUCYFKSBFREPBC-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 2
- 150000004056 anthraquinones Chemical class 0.000 description 2
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 description 2
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical class C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 2
- 238000012663 cationic photopolymerization Methods 0.000 description 2
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- 150000004696 coordination complex Chemical class 0.000 description 2
- 235000001671 coumarin Nutrition 0.000 description 2
- 230000001186 cumulative effect Effects 0.000 description 2
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- 150000001989 diazonium salts Chemical class 0.000 description 2
- VFHVQBAGLAREND-UHFFFAOYSA-N diphenylphosphoryl-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)P(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 VFHVQBAGLAREND-UHFFFAOYSA-N 0.000 description 2
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- IIPYXGDZVMZOAP-UHFFFAOYSA-N lithium nitrate Chemical compound [Li+].[O-][N+]([O-])=O IIPYXGDZVMZOAP-UHFFFAOYSA-N 0.000 description 2
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- SHXRPEYRCYQSFS-UHFFFAOYSA-N n-benzhydrylprop-2-enamide Chemical compound C=1C=CC=CC=1C(NC(=O)C=C)C1=CC=CC=C1 SHXRPEYRCYQSFS-UHFFFAOYSA-N 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
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- 230000035515 penetration Effects 0.000 description 2
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- 238000007639 printing Methods 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 description 2
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 2
- 125000004076 pyridyl group Chemical group 0.000 description 2
- 239000013557 residual solvent Substances 0.000 description 2
- 238000003892 spreading Methods 0.000 description 2
- 230000007480 spreading Effects 0.000 description 2
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical group C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 2
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 2
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- 239000001993 wax Substances 0.000 description 2
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- XVKKIGYVKWTOKG-UHFFFAOYSA-N diphenylphosphoryl(phenyl)methanone Chemical compound C=1C=CC=CC=1P(=O)(C=1C=CC=CC=1)C(=O)C1=CC=CC=C1 XVKKIGYVKWTOKG-UHFFFAOYSA-N 0.000 description 1
- MJNOICMZVNDXQA-UHFFFAOYSA-N diphenylphosphoryl(pyridin-3-yl)methanone Chemical compound C=1C=CC=CC=1P(=O)(C=1C=CC=CC=1)C(=O)C1=CC=CN=C1 MJNOICMZVNDXQA-UHFFFAOYSA-N 0.000 description 1
- UTZDKCFZGDSBGI-UHFFFAOYSA-N diphenylphosphoryl-(1-methylcyclohexyl)methanone Chemical compound C=1C=CC=CC=1P(=O)(C=1C=CC=CC=1)C(=O)C1(C)CCCCC1 UTZDKCFZGDSBGI-UHFFFAOYSA-N 0.000 description 1
- HZWAUDKTZOUQPD-UHFFFAOYSA-N diphenylphosphoryl-(2-methylphenyl)methanone Chemical compound CC1=CC=CC=C1C(=O)P(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 HZWAUDKTZOUQPD-UHFFFAOYSA-N 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 150000002019 disulfides Chemical class 0.000 description 1
- KGGOIDKBHYYNIC-UHFFFAOYSA-N ditert-butyl 4-[3,4-bis(tert-butylperoxycarbonyl)benzoyl]benzene-1,2-dicarboperoxoate Chemical compound C1=C(C(=O)OOC(C)(C)C)C(C(=O)OOC(C)(C)C)=CC=C1C(=O)C1=CC=C(C(=O)OOC(C)(C)C)C(C(=O)OOC(C)(C)C)=C1 KGGOIDKBHYYNIC-UHFFFAOYSA-N 0.000 description 1
- YMRYNEIBKUSWAJ-UHFFFAOYSA-N ditert-butyl benzene-1,3-dicarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC(C(=O)OOC(C)(C)C)=C1 YMRYNEIBKUSWAJ-UHFFFAOYSA-N 0.000 description 1
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- 239000003822 epoxy resin Substances 0.000 description 1
- IINNWAYUJNWZRM-UHFFFAOYSA-L erythrosin B Chemical compound [Na+].[Na+].[O-]C(=O)C1=CC=CC=C1C1=C2C=C(I)C(=O)C(I)=C2OC2=C(I)C([O-])=C(I)C=C21 IINNWAYUJNWZRM-UHFFFAOYSA-L 0.000 description 1
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- 229910017053 inorganic salt Inorganic materials 0.000 description 1
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- 229910052742 iron Inorganic materials 0.000 description 1
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 description 1
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- 150000005309 metal halides Chemical class 0.000 description 1
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical group CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 description 1
- CXKWCBBOMKCUKX-UHFFFAOYSA-M methylene blue Chemical compound [Cl-].C1=CC(N(C)C)=CC2=[S+]C3=CC(N(C)C)=CC=C3N=C21 CXKWCBBOMKCUKX-UHFFFAOYSA-M 0.000 description 1
- 229960000907 methylthioninium chloride Drugs 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- KMBPCQSCMCEPMU-UHFFFAOYSA-N n'-(3-aminopropyl)-n'-methylpropane-1,3-diamine Chemical compound NCCCN(C)CCCN KMBPCQSCMCEPMU-UHFFFAOYSA-N 0.000 description 1
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- RQAKESSLMFZVMC-UHFFFAOYSA-N n-ethenylacetamide Chemical compound CC(=O)NC=C RQAKESSLMFZVMC-UHFFFAOYSA-N 0.000 description 1
- ZQXSMRAEXCEDJD-UHFFFAOYSA-N n-ethenylformamide Chemical compound C=CNC=O ZQXSMRAEXCEDJD-UHFFFAOYSA-N 0.000 description 1
- KKFHAJHLJHVUDM-UHFFFAOYSA-N n-vinylcarbazole Chemical compound C1=CC=C2N(C=C)C3=CC=CC=C3C2=C1 KKFHAJHLJHVUDM-UHFFFAOYSA-N 0.000 description 1
- 239000000025 natural resin Substances 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- 150000002815 nickel Chemical class 0.000 description 1
- 229920001220 nitrocellulos Polymers 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000013307 optical fiber Substances 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 239000012860 organic pigment Substances 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- 150000002921 oxetanes Chemical class 0.000 description 1
- 125000003566 oxetanyl group Chemical group 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- FZUGPQWGEGAKET-UHFFFAOYSA-N parbenate Chemical compound CCOC(=O)C1=CC=C(N(C)C)C=C1 FZUGPQWGEGAKET-UHFFFAOYSA-N 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- LYXOWKPVTCPORE-UHFFFAOYSA-N phenyl-(4-phenylphenyl)methanone Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1C(=O)C1=CC=CC=C1 LYXOWKPVTCPORE-UHFFFAOYSA-N 0.000 description 1
- XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical class [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 150000003018 phosphorus compounds Chemical class 0.000 description 1
- 229920002120 photoresistant polymer Polymers 0.000 description 1
- 229940110337 pigment blue 1 Drugs 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920001281 polyalkylene Polymers 0.000 description 1
- 229920006122 polyamide resin Polymers 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
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- 229920005668 polycarbonate resin Polymers 0.000 description 1
- 239000004431 polycarbonate resin Substances 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
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- 229920000570 polyether Polymers 0.000 description 1
- 229920005749 polyurethane resin Polymers 0.000 description 1
- ZNNZYHKDIALBAK-UHFFFAOYSA-M potassium thiocyanate Chemical compound [K+].[S-]C#N ZNNZYHKDIALBAK-UHFFFAOYSA-M 0.000 description 1
- 229940116357 potassium thiocyanate Drugs 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 230000027756 respiratory electron transport chain Effects 0.000 description 1
- PYWVYCXTNDRMGF-UHFFFAOYSA-N rhodamine B Chemical compound [Cl-].C=12C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C2C=1C1=CC=CC=C1C(O)=O PYWVYCXTNDRMGF-UHFFFAOYSA-N 0.000 description 1
- 229940043267 rhodamine b Drugs 0.000 description 1
- 229940081623 rose bengal Drugs 0.000 description 1
- 229930187593 rose bengal Natural products 0.000 description 1
- STRXNPAVPKGJQR-UHFFFAOYSA-N rose bengal A Natural products O1C(=O)C(C(=CC=C2Cl)Cl)=C2C21C1=CC(I)=C(O)C(I)=C1OC1=C(I)C(O)=C(I)C=C21 STRXNPAVPKGJQR-UHFFFAOYSA-N 0.000 description 1
- VDNLFJGJEQUWRB-UHFFFAOYSA-N rose bengal free acid Chemical compound OC(=O)C1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1C1=C2C=C(I)C(=O)C(I)=C2OC2=C(I)C(O)=C(I)C=C21 VDNLFJGJEQUWRB-UHFFFAOYSA-N 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 239000004208 shellac Substances 0.000 description 1
- ZLGIYFNHBLSMPS-ATJNOEHPSA-N shellac Chemical compound OCCCCCC(O)C(O)CCCCCCCC(O)=O.C1C23[C@H](C(O)=O)CCC2[C@](C)(CO)[C@@H]1C(C(O)=O)=C[C@@H]3O ZLGIYFNHBLSMPS-ATJNOEHPSA-N 0.000 description 1
- 229940113147 shellac Drugs 0.000 description 1
- 235000013874 shellac Nutrition 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- 235000021286 stilbenes Nutrition 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical class [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 description 1
- 150000003464 sulfur compounds Chemical class 0.000 description 1
- 229910052714 tellurium Inorganic materials 0.000 description 1
- UWHCKJMYHZGTIT-UHFFFAOYSA-N tetraethylene glycol Chemical compound OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 1
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000012719 thermal polymerization Methods 0.000 description 1
- 150000004897 thiazines Chemical class 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- 235000010215 titanium dioxide Nutrition 0.000 description 1
- 229950003937 tolonium Drugs 0.000 description 1
- HNONEKILPDHFOL-UHFFFAOYSA-M tolonium chloride Chemical compound [Cl-].C1=C(C)C(N)=CC2=[S+]C3=CC(N(C)C)=CC=C3N=C21 HNONEKILPDHFOL-UHFFFAOYSA-M 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- PWBHRVGYSMBMIO-UHFFFAOYSA-M tributylstannanylium;acetate Chemical compound CCCC[Sn](CCCC)(CCCC)OC(C)=O PWBHRVGYSMBMIO-UHFFFAOYSA-M 0.000 description 1
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 description 1
- 125000005580 triphenylene group Chemical group 0.000 description 1
- 125000002348 vinylic group Chemical group 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 125000001834 xanthenyl group Chemical class C1=CC=CC=2OC3=CC=CC=C3C(C12)* 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D11/00—Inks
- C09D11/30—Inkjet printing inks
- C09D11/40—Ink-sets specially adapted for multi-colour inkjet printing
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D11/00—Inks
- C09D11/02—Printing inks
- C09D11/10—Printing inks based on artificial resins
- C09D11/101—Inks specially adapted for printing processes involving curing by wave energy or particle radiation, e.g. with UV-curing following the printing
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D11/00—Inks
- C09D11/30—Inkjet printing inks
- C09D11/32—Inkjet printing inks characterised by colouring agents
- C09D11/322—Pigment inks
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/24—Structurally defined web or sheet [e.g., overall dimension, etc.]
- Y10T428/24802—Discontinuous or differential coating, impregnation or bond [e.g., artwork, printing, retouched photograph, etc.]
Definitions
- the present invention relates to an ink composition suitably used for inkjet recording, an inkjet recording method and, furthermore, a printed material obtained by employing the ink composition and a process for producing a lithographic printing plate.
- an ink composition suitable for inkjet recording that enables inkjet recording to be carried out stably for a long period of time, cures with high sensitivity upon exposure to actinic radiation, and gives a cured material having sufficient flexibility even after the ink has been cured and having good adhesion to a recording medium; an inkjet recording method; a printed material employing same; and a process for producing a lithographic printing plate employing the ink composition.
- an image recording method for forming an image on a recording medium such as paper based on an image data signal
- an electrophotographic system there are an electrophotographic system, sublimation type and melt type thermal transfer systems, an inkjet system, etc.
- the electrophotographic system a process of forming an electrostatic latent image on a photosensitive drum by electrically charging and exposing is required, and the system is complicated; as a result, there is the problem that the production cost is high.
- the thermal transfer system although the equipment is inexpensive, due to the use of an ink ribbon there is the problem that the running cost is high and waste material is generated.
- the equipment is inexpensive and, since an image is formed directly on a recording medium by discharging an ink only on a required image area, the ink can be used efficiently and the running cost is low. Furthermore, there is little noise and it is excellent as an image recording system.
- JP-A-60-56557 and JP-A-57-156264 JP-A denotes a Japanese unexamined patent application publication
- JP-A denotes a Japanese unexamined patent application publication
- JP-A-2004-359946 describes an inkjet ink set that comprises at least a dark ink and a light ink and cures upon exposure to UV rays, wherein the inks constituting the inkjet ink set comprise at least a coloring material, a polymerizable compound, and a photopolymerization initiator, the concentration ratio of the coloring materials for the dark ink and the light ink is 2:1 to 10:1, and the concentration ratio of the photopolymerization initiators is 1:1 to 3:1.
- a light ink composition that has excellent curability and stability over time and gives a cured film having good flexibility, and an inkjet recording method, a printed material, and an ink set employing the ink composition.
- the ink composition (hereinafter, simply called an 'ink') of the present invention is an ink composition comprising (A) a pigment, (B) a polymerizable monomer, (C) a polymerization initiator, and (D) a dispersant, the content of the pigment being no greater than 1 wt % of the entire ink composition, and the ratio (D/A) of the weight A of the pigment to the weight D of the dispersant in the ink composition satisfying the relationship 0.5 ⁇ D/A ⁇ 15.
- the ink composition of the present invention is an ink composition with a small amount of pigment such that the content of the pigment is no greater than 1 wt % of the entire ink composition, and is also called a 'light ink composition' or a 'light ink'.
- the ink composition of the present invention is an ink composition that can cure upon exposure to radiation and is also an oil-based ink composition.
- the 'radiation' referred to in the present invention is not particularly limited as long as it is actinic radiation that can provide energy that enables an initiating species to be generated in the ink composition when irradiated, and broadly includes ⁇ rays, ⁇ rays, X rays, ultraviolet rays (UV), visible light, and an electron beam; among these, ultraviolet rays and an electron beam are preferable from the viewpoint of curing sensitivity and the availability of equipment, and ultraviolet rays are particularly preferable.
- the ink composition of the present invention is therefore preferably an ink composition that can cure upon exposure to ultraviolet rays as radiation.
- the ink composition of the present invention comprises a pigment.
- the pigment referred to here generally means a colorant that is sparingly soluble in various types of solvent (organic solvent, water), and in a normal ink composition it means one for which, of the total solids content of the colorant contained in the ink composition, the amount that dissolves in the ink composition is no greater than 10 wt %.
- the ink composition of the present invention has a pigment content of no greater than 1 wt % of the entire ink composition, preferably no greater than 0.7 wt %, more preferably no greater than 0.5 wt %, yet more preferably 0.01 to 0.5 wt %, and particularly preferably 0.2 to 0.5 wt %.
- the pigment that can be used in the present invention is not particularly limited, and a known pigment may be used.
- a compound that does not function as a polymerization inhibitor in a polymerization reaction, which is a curing reaction is preferably selected.
- the pigment that can be used in the present invention is not particularly limited and, for example, organic and inorganic pigments with the Color Index Nos. shown below may be used according to the intended purpose.
- Red or magenta pigments Pigment Red 3, 5, 19, 22, 31, 38, 42, 43, 48:1, 48:2, 48:3, 48:4, 48:5, 49:1, 53:1, 57:1, 57:2, 58:4, 63:1, 81, 81:1, 81:2, 81:3, 81:4, 88, 104, 108, 112, 122, 123, 144, 146, 149, 166, 168, 169, 170, 177, 178, 179, 184, 185, 208, 216, 226, and 257, Pigment Violet 3, 19, 23, 29, 30, 37, 50, and 88, and Pigment Orange 13, 16, 20, and 36.
- Pigment Blue 1 15, 15:1, 15:2, 15:3, 15:4, 15:6, 16, 17-1, 22, 27, 28, 29, 36, and 60.
- Green pigments Pigment Green 7, 26, 36, and 50.
- Yellow pigments Pigment Yellow 1, 3, 12, 13, 14, 17, 34, 35, 37, 55, 74, 81, 83, 93, 94, 95, 97, 108, 109, 110, 120, 137, 138, 139, 153, 154, 155, 157, 166, 167, 168, 180, 185, and 193.
- Black pigments Pigment Black 7, 28, and 26.
- White pigments Pigment White 6, 18, and 21.
- IRGALITE BLUE GLVO cyan pigment, manufactured by Ciba Specialty Chemicals
- CINQUASIA MAGENTA RT-335 D magenta pigment, manufactured by Ciba Specialty Chemicals
- NOVOPERM YELLOW H2G yellow pigment, manufactured by Clariant
- SPECIAL BLACK 250 black pigment, manufactured by Ciba Specialty Chemicals
- the pigment that can be used in the present invention is mixed with a dispersant and dispersed in a polymerizable monomer or is dispersed after mixing the polymerizable monomer and the dispersant.
- a dispersing machine such as a ball mill, a sand mill, an attritor, a roll mill, an agitator, a Henschel mixer, a colloidal mill, an ultrasonic homogenizer, a pearl mill, a wet type jet mill, or a paint shaker may be used.
- the pigment may be directly mixed with another component when preparing an ink composition or, in order to improve dispersion properties, it may be mixed after being added in advance to a dispersion medium such as a solvent or a polymerizable monomer used in the present invention and uniformly dispersing or dissolving it.
- a dispersion medium such as a solvent or a polymerizable monomer used in the present invention and uniformly dispersing or dissolving it.
- the colorant in order to prevent degradation of solvent resistance when there is residual solvent in a cured image and prevent the VOC (Volatile Organic Compound) problem due to residual solvent, the colorant is preferably added to a dispersion medium such as a polymerizable monomer and then mixed.
- a dispersion medium such as a polymerizable monomer
- These pigments may be used by appropriately selecting one type or two or more types according to the intended purpose of the ink composition.
- the pigment, the dispersant, and the dispersion medium are selected and for dispersion conditions and filtration conditions to be set so that the average particle size of pigment particles is preferably 0.005 to 0.5 ⁇ m, more preferably 0.01 to 0.45 ⁇ m, and yet more preferably 0.015 to 0.4 ⁇ m.
- the ratio by weight of the dispersant relative to the pigment when the weight of the pigment in the ink composition is A and the weight of the dispersant in the ink composition is D, the ratio by weight (D/A) is 0.5 ⁇ D/A ⁇ 15, preferably 1 ⁇ D/A ⁇ 10, and more preferably 1.2 ⁇ D/A ⁇ 8.
- the ratio by weight of the dispersant relative to the pigment exceeds 0.5, after being stored over time there is no aggregation/precipitation of the pigment, the ink viscosity does not increase, and an ink composition having excellent storage stability over time can thus be obtained.
- the ratio when the ratio is 15 or less, an ink composition having a low ink viscosity and excellent discharge properties can be obtained.
- the ink composition that can be used in the present invention comprises at least a polymerizable monomer.
- the polymerizable monomer that can be used in the present invention is preferably an addition-polymerizable compound, and more preferably a radically polymerizable compound or a cationically polymerizable compound.
- polymerizable compound that can be used in the present invention, one type may be used on its own, two or more types may be used or, for example, a radically polymerizable compound and a cationically polymerizable compound may be used in combination.
- the ink composition of the present invention preferably comprises a polymerizable monomer having at least one amide bond and/or aromatic group. Due to it containing the monomer, an ink composition having a pigment dispersion with excellent stability over time can be obtained. Although the reason for the effect being exhibited is not clear, it is surmised that the affinity between the pigment surface and a highly polar group such as an amide group or an aromatic group analogous to the pigment structure is high, thus decreasing the pigment surface energy and thereby giving a stable pigment dispersion.
- the monomer is particularly suitably used for a light ink for which it is difficult to maintain pigment dispersion stability.
- a polymerizable monomer having an amide bond As a radically polymerizable compound that can be used in the present invention, it is preferable to use a polymerizable monomer having an amide bond.
- a polymerizable monomer having an amide bond specifically preferred examples thereof include N -methyl- N -vinylformamide, N -methyl-N-vinylacetamide, N -vinylcarbazole, 1-vinylimidazole, N -cyclohexylacrylamide, N -(1,1-dimethyl-2-phenyl)ethylacrylamide, N -diphenylmethylacrylamide, N -phthalimidomethylacrylamide, N -(1,1'-dimethyl-3-(1,2,4-triazol-1-yl))propylacrylamide, 5-(meth)acryloyloxymethyl-5-ethyl-1,3-dioxacyclohexane, N -vinylformamide, N -
- n denotes an integer of 1 to 5; n is preferably an integer of 2 to 4 from the viewpoint of flexibility after the ink composition is cured, adhesion to a recording medium, and ready availability of starting materials, n is more preferably 2 or 4, and n is particularly preferably 4, which is N -vinylcaprolactam. N -Vinylcaprolactam is preferable since it has excellent safety, is commonly used and is readily available at a relatively low price, and gives particularly good ink curability and adhesion of a cured film to a recording medium.
- the N -vinyllactam may have a substituent such as an alkyl group or an aryl group on the lactam ring, and may have a saturated or unsaturated ring structure bonded to the lactam ring.
- the N -vinyllactam is a compound having a relatively high melting point, when the N -vinyllactam is used, if the content thereof in the ink composition is no greater than 40 wt %, good solubility is exhibited at a low temperature of 0°C or below, and the temperature range in which the ink composition can be handled becomes large.
- a radically polymerizable compound that can be used in the present invention, it is preferable to use a polymerizable monomer having an aromatic group.
- Preferred examples of the aromatic group include a phenyl group, a naphthyl group, an anthracenyl group, and a pyridinyl group.
- radically polymerizable monomer having an aromatic group examples include the compounds below (R-P-1 to 9, and N-1 to 28).
- R-P-1 to 9, and N-1 to 28 are examples of the radically polymerizable monomer having an aromatic group.
- a hydrocarbon chain is represented by a simplified structural formula in which symbols for carbon (C) and hydrogen (H) are omitted.
- the radically polymerizable compound it is also preferable to use a monomer having a cyclic structure other than an aromatic group.
- a monomer having a cyclic structure other than an aromatic group By containing a monomer having a cyclic structure other than an aromatic group, an ink composition having excellent curability can be obtained.
- cyclic monomer examples include a monomer having a cyclic hydrocarbon group such as a cyclohexyl group, a cyclopentyl group, a cycloheptyl group, an isobornyl group, or a tricyclodecanyl group, and a monomer having a heterocyclic group such as a tetrahydrofurfuryl group or a piperidinyl group.
- a cyclic hydrocarbon group such as a cyclohexyl group, a cyclopentyl group, a cycloheptyl group, an isobornyl group, or a tricyclodecanyl group
- heterocyclic group such as a tetrahydrofurfuryl group or a piperidinyl group.
- Preferred examples of a cyclic monomer having an acryloxy group, a methacryloxy group, and/or an acrylamide group include norbornyl (meth)acrylate, isobornyl (meth)acrylate, cyclohexyl (meth)acrylate, cyclopentyl (meth)acrylate, cycloheptyl (meth)acrylate, cyclooctyl (meth)acrylate, cyclodecyl (meth)acrylate, dicyclodecyl (meth)acrylate, trimethylcyclohexyl (meth)acrylate, 4-t-butylcyclohexyl (meth)acrylate, acryloylmorpholine, 2-benzyl (meth)acrylate, phenoxyethyl (meth)acrylate, phenoxydiethylene glycol (meth)acrylate, phenoxytriethylene glycol (meth)acrylate, ethylene oxide (EO)-modified cresol (meth)
- a cyclic monomer having an acryloxy group, a methacryloxy group, an acrylamide group, a methacrylamide group, and/or a vinyloxy group include compounds (M-1) to (M-29) below.
- an acyclic monofunctional monomer described below may be used in combination as necessary.
- the acyclic monofunctional monomer has relatively low viscosity and may be used preferably for the purpose of decreasing the viscosity of the composition.
- the proportion of the acyclic monofunctional monomer below in the entire composition is preferably no greater than 20 wt %, more preferably no greater than 15 wt %, and particularly preferably no greater than 10 wt %.
- Specific examples thereof include octyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, decyl (meth)acrylate, dodecyl (meth)acrylate, tridecyl (meth)acrylate, tetradecyl (meth)acrylate, hexadecyl (meth)acrylate, 2-hydroxyethyl (meth)acrylate, butoxyethyl (meth)acrylate, carbitol (meth)acrylate, 2-ethylhexyl diglycol (meth)acrylate, polyethylene glycol (meth)acrylate monomethyl ether, polypropylene glycol (meth)acrylate monomethyl ether, and polytetraethylene glycol (meth)acrylate monomethyl ether.
- a polyfunctional monomer described below may be used in combination as necessary.
- a composition having excellent curability and a high cured film strength is obtained.
- the proportion of the polyfunctional monomer in the entire composition is preferably no greater than 15 wt %, more preferably no greater than 10 wt %, and particularly preferably no greater than 5 wt %.
- Specific examples thereof include bis(4-(meth)acryloxypolyethoxyphenyl)propane, neopentyl glycol di(meth)acrylate, 1,6-hexanediol di(meth)acrylate, 1,9-nonanediol di(meth)acrylate, ethylene glycol di(meth)acrylate, diethylene glycol di(meth)acrylate, triethylene glycol di(meth)acrylate, tetraethylene glycol di(meth)acrylate, polyethylene glycol di(meth)acrylate, polypropylene glycol di(meth)acrylate, pentaerythritol tri(meth)acrylate, pentaerythritol tetra(meth)acrylate, dipentaerythritol tetra(meth)acrylate, trimethylolpropane tri(meth)acrylate, tetramethylolmethane tetra(meth)acrylate, t
- the cationically polymerizable compound that can be used in the present invention is not particularly limited as long as it is a compound for which a polymerization reaction is initiated by a cationic polymerization initiating species generated from a cationic polymerization initiator, which is described later, and that cures, and various types of cationically polymerizable monomers known as cationically photopolymerizable monomers may be used.
- Preferred examples of the cationically polymerizable monomers include epoxy compounds, vinyl ether compounds, and oxetane compounds described in JP-A-6-9714 , JP-A-2001-31892 , JP-A-2001-40068 , JP-A-2001-55507 , JP-A-2001-310938 , JP-A-2001-310937 , and JP-A-2001-220526 .
- a cationic polymerization type photocuring resin for example, a cationic polymerization type photocuring resin is known, and in recent years cationic photopolymerization type photocuring resins that have been sensitized in a visible light wavelength region of 400 nm or greater have also been disclosed in, for example, JP-A-6-43633 and JP-A-8-324137 .
- a cationically polymerizable compound that can be used in the present invention it is preferable to use a polymerizable monomer having an amide bond.
- Examples of the cationically polymerizable monomer having an amide bond include compounds (C-A-1) to (C-A-5) below.
- a cationically polymerizable compound that can be used in the present invention, it is preferable to use a polymerizable monomer having an aromatic group.
- aromatic group examples include a phenyl group, a naphthyl group, an anthracenyl group, and a pyridinyl group.
- Examples of the cationically polymerizable monomer having an aromatic group include compounds (C-P-1) to (C-P-6) below.
- the polymerizable monomer in the ink composition that can be used in the present invention is preferably 60 to 95 wt % relative to the total amount of the ink composition, more preferably 65 to 90 wt %, and yet more preferably 70 to 90 wt %. It is preferable for it to be in the above-mentioned range since the curability is excellent and the viscosity is appropriate.
- the polymerizable monomers in the ink composition that can be used in the present invention, it is preferable for at least one thereof to be a monofunctional monomer; when radically polymerizable monofunctional monomers are used at least one thereof is preferably a monofunctional (meth)acrylate, and it is more preferable for at least one thereof to be a monofunctional acrylate. It is preferable to use a monofunctional monomer since sufficient curability as well as sufficient flexibility of a cured film can be obtained.
- the proportion of the monofunctional radically polymerizable monomer in the composition is preferably 50 to 90 wt %, more preferably 55 to 85 wt %, and yet more preferably 65 to 80 wt %. It is preferable for the proportion to be in the above-mentioned range since the curability and the flexibility are excellent and the viscosity is appropriate.
- the proportion of the monofunctional cationically polymerizable monomer in the composition is preferably 30 to 90 wt %, more preferably 35 to 85 wt %, and yet more preferably 40 to 85 wt %. It is preferable for the proportion to be in the above-mentioned range since the curability and the flexibility are excellent and the viscosity is appropriate.
- the proportion of the di- or higher-functional monomer is preferably 0.5 to 50 wt %, more preferably 0.5 to 30 wt %, and yet more preferably 0.5 to 20 wt %. It is preferable for the proportion to be in the above-mentioned range since the curability and the flexibility are excellent and the viscosity is appropriate.
- the ink composition of the present invention preferably comprises a radically polymerizable monomer having an amide bond, a radically polymerizable monomer having an aromatic group, and a radically polymerizable monomer having a cyclic structure other than an aromatic group, or a cationically polymerizable monomer having an epoxy group, a cationically polymerizable monomer having an oxetanyl group, and a cationically polymerizable monomer having an amide bond and/or a cationically polymerizable monomer having an aromatic group.
- the ink when it is cured using actinic radiation such as ultraviolet rays, it comprises a polymerization initiator.
- a polymerization initiator that can be used in the present invention a known polymerization initiator may be used, and it is preferable to use a radical polymerization initiator.
- the polymerization initiator that can be used in the present invention may be used singly or in a combination of two or more types.
- the radical polymerization initiator may be used in combination with a cationic polymerization initiator.
- the polymerization initiator that can be used in the ink composition of the present invention is a compound that forms a polymerization initiating species by absorbing external energy.
- the external energy used for initiating polymerization can be broadly divided into heat and actinic radiation, and a thermal polymerization initiator and a photopolymerization initiator are used respectively.
- Examples of the actinic radiation include ⁇ rays, ⁇ rays, an electron beam, ultraviolet rays, visible light, and infrared rays.
- the external energy used for initiating polymerization is preferably actinic radiation, more preferably the electron beam or ultraviolet rays, and yet more preferably ultraviolet rays.
- radical polymerization initiator examples include (a) an aromatic ketone, (b) an acylphosphine compound, (c) an aromatic onium salt compound, (d) an organic peroxide, (e) a thio compound, (f) a hexaarylbiimidazole compound, (g) a ketoxime ester compound, (h) a borate compound, (i) an azinium compound, (j) a metallocene compound, (k) an active ester compound, (I) a compound having a carbon-halogen bond, and (m) an alkylamine compound.
- radical polymerization initiators the above-mentioned compounds (a) to (m) may be used singly or in combination.
- the radical polymerization initiator in the present invention may suitably be used singly or in a combination of two or more types.
- Preferred examples of the aromatic ketone (a) and the thio compound (e) include a compound having a benzophenone skeleton (benzophenone compound) or a compound having a thioxanthone skeleton (thioxanthone compound) described in 'RADIATION CURING IN POLYMER SCIENCE AND TECHNOLOGY' J. P. FOUASSIER and J. F. RABEK (1993), pp. 77 to 117 .
- Preferred examples of the aromatic ketone (a), the acylphosphine compound (b), and the thio compound (e) include an ⁇ -thiobenzophenone compound described in JP-B-47-6416 , a benzoin ether compound described in JP-B-47-3981 , an ⁇ -substituted benzoin compound described in JP-B-47-22326 , a benzoin derivative described in JP-B-47-23664 , an aroylphosphonic acid ester described in JP-A-57-30704 , a dialkoxybenzophenone described in JP-B-60-26483 , benzoin ethers described in JP-B-60-26403 and JP-A-62-81345 , ⁇ -aminobenzophenones described in JP-B-1-34242 , US Pat.
- benzophenone compound examples include benzophenone, 4-phenylbenzophenone, isophthalophenone, and 4-benzoyl-4'-methylphenylsulfide.
- benzophenone compound it is also preferable to use a diaminobenzophenone compound.
- diaminobenzophenone compound examples include p,p'-tetramethyldiaminobenzophenone.
- Examples of the thioxanthone compound include 2,4-diethylthioxanthone, 2-isopropylthioxanthone, and 2-chlorothioxanthone.
- the aromatic ketone (a) is preferably an ⁇ -hydroxyketone, and examples thereof include 1-[4-(2-hyd roxyethoxy)phenyl]-2-hyd roxy-2-methyl-1-propan-1-one, 2-hydroxy-2-methyl-1-phenylpropan-1-one, and 1-hydroxycyclohexyl phenyl ketone.
- the aromatic ketone (a) is particularly preferably a 1-hydroxycyclohexyl phenyl ketone compound.
- the 1-hydroxycyclohexyl phenyl ketone compound referred to in the present invention means 1-hydroxycyclohexyl phenyl ketone and a compound obtained by substituting 1-hydroxycyclohexyl phenyl ketone with any substituent.
- the substituent may be selected freely from a range that enables an ability as a radical polymerization initiator to be exhibited, and specific examples thereof include an alkyl group (e.g. a methyl group, an ethyl group, a propyl group, a butyl group, etc.).
- the acylphosphine compound (b) is preferably an acylphosphine oxide compound.
- acylphosphine oxide compound examples include a compound having a structure represented by Formula (7) or (8).
- the acylphosphine oxide compound is particularly preferably one having a chemical structure represented by Formula (9) or (10).
- R 6 , R 7 , and R 8 denote an aromatic hydrocarbon group, which may have a methyl group or an ethyl group as a substituent.
- R 9 , R 10 , and R 11 denote an aromatic hydrocarbon group, which may have a methyl group or an ethyl group as a substituent.
- acylphosphine oxide compound a monoacylphosphine oxide compound, a bisacylphosphine oxide compound, etc. may be used, and as the monoacylphosphine oxide compound, a known monoacylphosphine oxide compound may be used. Examples thereof include monoacylphosphine oxide compounds described in JP-B-60-8047 and JP-B-63-40799 .
- methyl isobutyrylmethylphosphinate methyl isobutyrylphenylphosphinate, methyl pivaloylphenylphosphinate, methyl 2-ethylhexanoylphenylphosphinate, isopropyl pivaloylphenylphosphinate, methyl p-tolylphenylphosphinate, methyl o-tolylphenylphosphinate, methyl 2,4-dimethylbenzoylphenylphosphinate, isopropyl p-t-butylbenzoylphenylphosphinate, methyl acryloylphenylphosphinate, isobutyryldiphenylphosphine oxide, 2-ethylhexanoyldiphenylphosphine oxide, o-tolyldiphenylphosphine oxide, p-t-butylbenzoyldiphenylphosphine oxide, 3-pyri
- the bisacylphosphine oxide compound a known bisacylphosphine oxide compound may be used. Examples thereof include bisacylphosphine oxide compounds described in JP-A-3-101686 , JP-A-5-345790 , and JP-A-6-298818 .
- bis(2,6-dichlorobenzoyl)phenylphosphine oxide bis(2,6-dichlorobenzoyl)-2,5-dimethylphenylphosphine oxide, bis(2,6-dichlorobenzoyl)-4-ethoxyphenylphosphine oxide, bis(2,6-dichlorobenzoyl)-4-propylphenylphosphine oxide, bis(2,6-dichlorobenzoyl)-2-naphthylphosphine oxide, bis(2,6-dichlorobenzoyl)-1-naphthylphosphine oxide, bis(2,6-dichlorobenzoyl)-4-chlorophenylphosphine oxide, bis(2,6-dichlorobenzoyl)-2,4-dimethoxyphenylphosphine oxide, bis(2,6-dichlorobenzoyl)decylphosphine oxide, bis
- acylphosphine oxide compound in the present invention include bis(2,4,6-trimethylbenzoyl)phenylphosphine oxide (Irgacure 819: manufactured by Ciba Specialty Chemicals), bis(2,6-dimethoxybenzoyl)-2,4,4-trimethylpentylphenylphosphine oxide, and 2,4,6-trimethylbenzoyldiphenylphosphine oxide (Darocur TPO: manufactured by Ciba Specialty Chemicals, Lucirin TPO: manufactured by BASF).
- aromatic onium salt compound (c) there can be cited aromatic onium salts of elements of Groups 15, 16, and 17 of the periodic table, specifically, N, P, As, Sb, Bi, 0, S, Se, Te, and 1. Examples thereof include iodonium salts described in EP No. 104143 , US Pat. No. 4837124 , JP-A-2-150848 , and JP-A-2-96514 , diazonium salts (optionally substituted benzenediazoniums, etc.) described in EP Nos. 370693 , 233567 , 297443 , 297442 , 279210 , and 422570 , US Pat. Nos.
- diazonium salt resins diazodiphenylamine formaldehyde resins, etc.
- N -alkoxypyridinium salts etc.
- JP-A-63-138345 JP-A-63-142345 , JP-A-63-142346 , and JP-B-46-42363 ; specific examples thereof include 1-methoxy-4-phenylpyridinium tetrafluoroborate); furthermore, compounds described in JP-B-52-147277 , 52-14278 , and 52-14279 may suitably be used.
- a radical or an acid is formed as an active species.
- organic peroxide (d) almost all organic compounds having at least one oxygen-oxygen bond per molecule can be cited, and preferred examples thereof include peroxide ester compounds such as 3,3',4,4'-tetra(t-butylperoxycarbonyl)benzophenone, 3,3',4,4'-tetra(t-amylperoxycarbonyl)benzophenone, 3,3',4,4'-tetra(t-hexylperoxycarbonyl)benzophenone, 3,3',4,4'-tetra(t-octylperoxycarbonyl)benzophenone, 3,3',4,4'-tetra(cumylperoxycarbonyl)benzophenone, 3,3',4,4'-tetra(p-isopropylcumylperoxycarbonyl)benzophenone, and di-t-butyldiperoxyisophthalate.
- peroxide ester compounds such as 3,3',4,4'-tetra(t
- lophine dimers described in JP-B-45-37377 and JP-B-44-86516 there can be cited lophine dimers described in JP-B-45-37377 and JP-B-44-86516 , and examples thereof include 2,2'-bis(o-chlorophenyl)-4,4',5,5'-tetraphenylbiimidazole, 2,2'-bis(o-bromophenyl)-4,4',5,5'-tetraphenylbiimidazole, 2,2'-bis(o,p-dichlorophenyl)-4,4',5,5'-tetraphenylbiimidazole, 2,2'-bis(o-chlorophenyl)-4,4',5,5'-tetra(m-methoxyphenyl)biimidazole, 2,2'-bis(o,o'-dichlorophenyl)-4,4',5,5'-tetrapheny
- ketoxime ester compound (g) there can be cited 3-benzoyloxyiminobutan-2-one, 3-acetoxyiminobutan-2-one, 3-propionyloxyiminobutan-2-one, 2-acetoxyiminopentan-3-one, 2-acetoxyimino-1-phenylpropan-1-one, 2-benzoyloxyimino-1-phenylpropan-1-one, 3-p-toluenesulfonyloxyiminobutan-2-one, and 2-ethoxycarbonyloxyimino-1-phenylpropan-1-one.
- borate compound (h) examples include compounds described in US Pat. Nos. 3,567,453 and 4,343,891 , and EP Nos. 109,772 and 109,773 .
- Examples of the azinium salt compound (i) include N-O bond-containing compounds described in JP-A-63-138345 , JP-A-63-142345 , JP-A-63-142346 , JP-A-63-143537 , and JP-B-46-42363 .
- metallocene compound (j) examples include titanocene compounds described in JP-A-59-152396 , JP-A-61-151197 , JP-A-63-41484 , JP-A-2-249 , and JP-A-2-4705 , and iron-arene complexes described in JP-A-1-304453 and JP-A-1-152109 .
- titanocene compound examples include dichlorobis(cyclopentadienyl)titanium, bis(cyclopentadienyl)bis(phenyl)titanium, bis(cyclopentadienyl)bis(2,3,4,5,6-pentafluorophen-1-yl)titanium, bis(cyclopentadienyl)bis(2,3,5,6-tetrafluorophen-1-yl)titanium, bis(cyclopentadienyl)bis(2,4,6-trifluorophen-1-yl)titanium, bis(cyclopentadienyl)bis(2,6-difluorophen-1-yl)titanium, bis(cyclopentadienyl)bis(2,4-difluorophen-1-yl)titanium, bis(methylcyclopentadienyl)bis(2,3,4,5,6-pentafluorophen-1-yl)titanium
- Examples of the active ester compound (k) include nitrobenzyl ester compounds described in EP Nos. 0290750 , 046083 , 156153 , 271851 , and 0388343 , US Pat. Nos. 3901710 and 4181531 , JP-A-60-198538 , and JP-A-53-133022 , iminosulfonate compounds described in EP Nos. 0199672 , 84515 , 199672 , 044115 , and 0101122 , US Pat. Nos.
- Preferred examples of the compound (I) having a carbon-halogen bond include a compound described in Wakabayashi et. al, Bull. Chem. Soc. Japan, 42, 2924 (1969 ), a compound described in British Patent No. 1388492 , a compound described in JP-A-53-133428 , and a compound described in German Patent No. 3337024 .
- alkylamine compound (m) examples include an alkylenediamine (ethylenediamine, tetramethylenediamine, hexamethylenediamine, etc.), a polyalkylene (alkylene having 2 to 6 carbons) polyamine (diethylenetriamine, triethylenetetramine, pentaethylenehexamine, iminobispropylamine, bis(hexamethylene)triamine, etc.), an alkyl- or hydroxyalkyl-amine compound (an alkyl (having 1 to 3 carbons) aminopropylamine, aminoethylethanolamine, methyliminobispropylamine, etc.), N-aminoethylpiperazine, 1,3-diaminocyclohexane, isophoronediamine, hydrogenated methylenedianiline, 3,9-bis(3-aminopropyl)-2,4,8,10-tetraoxaspiro[5.5]undecane, N,N-dimethylcyclo
- Examples further include a compound described in F. C. Schaefer et al., J. Org. Chem., 29, 1527 (1964 ), a compound described in JP-A-62-58241 , a compound described in JP-A-5-281728 , a compound described in German Pat. No. 2641100 , a compound described in German Pat. No. 3333450 , compounds described in German Pat. No. 3021590 , and compounds described in German Pat. No. 3021599 .
- a cationic polymerization initiator When a cationically polymerizable compound is used in the present invention, it is preferable to use a cationic polymerization initiator.
- the cationic polymerization initiator photo-acid generator
- examples of the cationic polymerization initiator (photo-acid generator) that can be used in the present invention include chemically amplified photoresists and compounds used in cationic photopolymerization ( 'Imejingu you Yukizairyou' (Organic Materials for Imaging), Ed. The Japanese Research Association for Organic Electronics Materials, Bunshin Publishing Co. (1993), pp. 187-192 ).
- Preferred examples of the cationic polymerization initiator in the present invention are listed below.
- B(C 6 F 5 ) 4 - , PF 6 - , AsF 6 - , SbF 6 - , and CF 3 SO 3 - salts of diazonium, ammonium, iodonium, sulfonium, phosphonium, etc. aromatic onium compounds can be cited.
- sulfonated materials that generate a sulfonic acid can be cited.
- halides that photogenerate a hydrogen halide can also be used.
- iron arene complexes can be cited.
- the total amount of polymerization initiator used is preferably 0.01 to 35 wt % relative to the total amount of polymerizable compound used, more preferably 0.5 to 20 wt %, and yet more preferably 1.0 to 15 wt %.
- the ink composition can be cured sufficiently with 0.01 wt % or greater of the polymerization initiator, and a cured film having a uniform degree of curing can be obtained with 35 wt % or less.
- the total amount of polymerization initiator used is preferably 200:1 to 1:200 relative to the sensitizer as a ratio by weight of polymerization initiator : sensitizer, more preferably 50:1 to 1:50, and yet more preferably 20:1 to 1:5.
- the ink composition of the present invention comprises a dispersant in order to stably disperse the pigment in the ink composition.
- a polymeric dispersant As the dispersant that can be used in the present invention, a polymeric dispersant is preferable.
- the 'polymeric dispersant' referred to in the present invention means a dispersant having a weight-average molecular weight of 1,000 or greater.
- the dispersant that can be used in the present invention is preferably a polymeric dispersant having a weight-average molecular weight of 2,000 to 50,000, and more preferably a polymeric dispersant having a weight-average molecular weight of 3,000 to 30,000.
- the weight-average molecular weight is 2,000 or greater, excellent pigment dispersibility can be obtained, and when the weight-average molecular weight is no greater than 50,000, an ink composition having excellent continuous discharge stability can be obtained.
- polymeric dispersant examples include polymeric dispersants such as DisperBYK-101, DisperBYK-102, DisperBYK-103, DisperBYK-106, DisperBYK-111, DisperBYK-161, DisperBYK-162, DisperBYK-163, DisperBYK-164, DisperBYK-166, DisperBYK-167, DisperBYK-168, DisperBYK-170, DisperBYK-171, DisperBYK-174, and DisperBYK-182 (all manufactured by BYK Chemie), EFKA4010, EFKA4046, EFKA4080, EFKA5010, EFKA5207, EFKA5244, EFKA6745, EFKA6750, EFKA7414, EFKA745, EFKA7462, EFKA7500, EFKA7570, EFKA7575, and EFKA7580 (all manufactured by EFKA Additives), Disperse Aid 6, Dis
- the content of the dispersant in the ink composition of the present invention is appropriately selected according to the intended purpose, and is generally preferably 0.05 to 15 wt % relative to the weight of the entire ink composition.
- the ink composition of the present invention may comprise another component as necessary.
- the other component include a sensitizer, a cosensitizer, another polymerizable compound, a surfactant, a UV absorber, an antioxidant, an antifading agent, a conductive salt, a solvent, a polymer compound, and a basic compound.
- the ink composition of the present invention may contain a sensitizer in order to promote decomposition of the above-mentioned polymerization initiator by absorbing specific actinic radiation, in particular when used for inkjet recording.
- the sensitizer absorbs specific actinic radiation and attains an electronically excited state.
- the sensitizer in the electronically excited state causes actions such as electron transfer, energy transfer, or heat generation upon contact with the polymerization initiator. This causes the polymerization initiator to undergo a chemical change and decompose, thus forming a radical, an acid, or a base.
- sensitizer in the ink composition of the present invention, it is preferable to use a sensitizing dye.
- Preferred examples of the sensitizing dye include those that belong to compounds below and have an adsorption wavelength in the region of 350 nm to 450 nm.
- Polynuclear aromatic compounds e.g. pyrene, perylene, triphenylene
- xanthenes e.g. fluorescein, eosin, erythrosine, rhodamine B, rose bengal
- cyanines e.g. thiacarbocyanine, oxacarbocyanine
- merocyanines e.g. merocyanine, carbomerocyanine
- thiazines e.g. thionine, methylene blue, toluidine blue
- acridines e.g. acridine orange, chloroflavin, acriflavine
- anthraquinones e.g. anthraquinone
- squaryliums e.g. squarylium
- coumarins e.g. 7-diethylamino-4-methylcoumarin
- Preferred examples of the sensitizing dye include compounds represented by Formulae (IX) to (XIII) below.
- a 1 denotes a sulfur atom or NR 50
- R 50 denotes an alkyl group or an aryl group
- L 2 denotes a non-metallic atomic group forming a basic nucleus of a dye in cooperation with a neighboring A 1 and the neighboring carbon atom
- R 51 and R 52 independently denote a hydrogen atom or a monovalent non-metallic atomic group
- R 51 and R 52 may be bonded together to form an acidic nucleus of a dye.
- W denotes an oxygen atom or a sulfur atom.
- Ar 1 and Ar 2 independently denote an aryl group and are connected to each other via a bond of -L 3 -.
- L 3 denotes -O- or -S-.
- W has the same meaning as that shown in Formula (IX).
- a 2 denotes a sulfur atom or NR 59
- L 4 denotes a non-metallic atomic group forming a basic nucleus of a dye in cooperation with the neighboring A 2 and carbon atom
- R 53 , R 54 , R 55 , R 56 , R 57 , and R 58 independently denote a monovalent non-metallic atomic group
- R 59 denotes an alkyl group or an aryl group.
- a 3 and A 4 independently denote -S-, -NR 62 -, or -NR 63 -, R 62 and R 63 independently denote a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group, L 5 and L 6 independently denote a non-metallic atomic group forming a basic nucleus of a dye in cooperation with the neighboring A 3 and A 4 and neighboring carbon atom, and R 60 and R 61 independently denote a hydrogen atom or a monovalent non-metallic atomic group, or are bonded to each other to form an aliphatic or aromatic ring.
- R 66 denotes an aromatic ring or a hetero ring, which may have a substituent
- a 5 denotes an oxygen atom, a sulfur atom, or -NR 67 -.
- R 64 , R 65 , and R 67 independently denote a hydrogen atom or a monovalent non-metallic atomic group, and R 67 and R 64 , and R 65 and R 67 may be bonded to each other to form an aliphatic or aromatic ring.
- the content of the sensitizer in the ink composition of the present invention is appropriately selected according to the intended purpose, but it is generally preferably 0.05 to 4 wt % relative to the weight of the entire ink composition.
- the ink composition of the present invention preferably comprises a cosensitizer.
- the cosensitizer has the function of further improving the sensitivity of the sensitizing dye to actinic radiation or the function of suppressing inhibition by oxygen of polymerization of a polymerizable compound, etc.
- Examples of such a cosensitizer include amines such as compounds described in M. R. Sander et al., 'Journal of Polymer Society', Vol. 10, p. 3173 (1972 ), JP-B-44-20189 , JP-A-51-82102 , JP-A-52-134692 , JP-A-59-138205 , JP-A-60-84305 , JP-A-62-18537 , JP-A-64-33104 , and Research Disclosure No. 33825, and specific examples thereof include triethanolamine, ethyl p-dimethylaminobenzoate, p-formyldimethylaniline, and p-methylthiodimethylaniline.
- cosensitizer examples include thiols and sulfides such as thiol compounds described in JP-A-53-702 , JP-B-55-500806 , and JP-A-5-142772 , and disulfide compounds of JP-A-56-75643 , and specific examples thereof include 2-mercaptobenzothiazole, 2-mercaptobenzoxazole, 2-mercaptobenzimidazole, 2-mercapto-4(3H)-quinazoline, and ⁇ -mercaptonaphthalene.
- cosensitizer examples include amino acid compounds (e.g. N-phenylglycine, etc.), organometallic compounds described in JP-B-48-42965 (e.g. tributyltin acetate, etc.), hydrogen-donating compounds described in JP-B-55-34414 , sulfur compounds described in JP-A-6-308727 (e.g. trithiane, etc.), phosphorus compounds described in JP-A-6-250387 (diethylphosphite, etc.), and Si-H, Ge-H compounds described in JP-A-8-54735 .
- amino acid compounds e.g. N-phenylglycine, etc.
- organometallic compounds described in JP-B-48-42965 e.g. tributyltin acetate, etc.
- hydrogen-donating compounds described in JP-B-55-34414 examples include sulfur compounds described in JP-A-6-308727 (e.g. trithiane, etc.
- the content of the cosensitizer in the ink composition of the present invention is appropriately selected according to the intended purpose, but it is generally preferably 0.05 to 4 wt % relative to the weight of the entire ink composition.
- a surfactant to the ink composition of the present invention in order to impart long-term discharge stability.
- surfactant those described in JP-A-62-173463 and 62-183457 can be cited.
- anionic surfactants such as dialkylsulfosuccinic acid salts, alkylnaphthalene sulfonic acid salts, and fatty acid salts
- nonionic surfactants such as polyoxyethylene alkyl ethers, polyoxyethylene alkyl aryl ethers, acetylene glycols, and polyoxyethylene/polyoxypropylene block copolymers
- cationic surfactants such as alkylamine salts and quaternary ammonium salts.
- An organofluoro compound may be used instead of the above-mentioned surfactant.
- the organofluoro compound is preferably hydrophobic.
- examples of the organofluoro compound include fluorine-based surfactants, oil-like fluorine-based compounds (e.g. fluorine oil), solid fluorine compound resins (e.g. tetrafluoroethylene resin), and those described in JP-B-57-9053 (paragraphs 8 to 17) and JP-A-62-135826 .
- the content of the surfactant in the ink composition of the present invention is appropriately selected according to the intended purpose and is generally preferably 0.0001 to 1 wt % relative to the weight of the entire ink composition.
- a UV absorber may be used from the viewpoint of improving the weather resistance of an image obtained and preventing discoloration.
- the UV absorbers include benzotriazole compounds described in JP-A-58-185677 , JP-A-61-190537 , JP-A-2-782 , JP-A-5-197075 and JP-A-9-34057 ; benzophenone compounds described in JP-A-46-2784 , JP-A-5-194483 and US Pat. No.
- JP-W as used herein means an unexamined published international patent application
- compounds described in Research Disclosure No. 24239 and compounds represented by stilbene and benzoxazole compounds, which absorb ultraviolet rays to emit fluorescence, the so-called fluorescent brightening agents.
- the amount thereof added is appropriately selected according to the intended application, and it is generally on the order of 0.5 to 15 wt % on the basis of the solids content in the ink composition.
- an antioxidant may be added.
- the antioxidant include those described in Laid-open European Patent Nos. 223739 , 309401 , 309402 , 310551 , 310552 , and 459416 , Laid-open German Patent No. 3435443 , JP-A-54-48535 , JP-A-62-262047 , JP-A-63-113536 , JP-A-63-163351 , JP-A-2-262654 , JP-A-2-71262 , JP-A-3-121449 , JP-A-5-61166 , JP-A-5-119449 , and US Pat. Nos. 4,814,262 and 4,980,275 .
- the amount thereof added is appropriately selected according to the intended application, and it is preferably on the order of 0.1 to 8 wt % on the basis of the solids content in the ink composition.
- the ink composition of the present invention may employ various organic and metal complex antifading agents.
- the organic antifading agents include hydroquinones, alkoxyphenols, dialkoxyphenols, phenols, anilines, amines, indanes, chromans, alkoxyanilines, and heterocycles
- the metal complex antifading agents include nickel complexes and zinc complexes. More specifically, there can be used compounds described in patents cited in Research Disclosure, No. 17643, Items VII-I to J, ibid., No.15162, ibid., No.18716, page 650, left-hand column, ibid., No. 36544, page 527, ibid., No. 307105, page 872, and ibid., No. 15162, and compounds contained in general formulae and compound examples of typical compounds described in JP-A-62-21572 , pages 127 to 137.
- the amount thereof added is appropriately selected according to the intended application, and it is preferably on the order of 0.1 to 8 wt % on the basis of the solids content in the ink composition.
- the ink composition of the present invention may contain, for the purpose of controlling discharge properties, a conductive salt such as potassium thiocyanate, lithium nitrate, ammonium thiocyanate, or dimethylamine hydrochloride.
- a conductive salt such as potassium thiocyanate, lithium nitrate, ammonium thiocyanate, or dimethylamine hydrochloride.
- the solvent examples include ketone-based solvents such as acetone, methyl ethyl ketone, and diethyl ketone, alcohol-based solvents such as methanol, ethanol, 2-propanol, 1-propanol, 1-butanol, and tert-butanol, chlorine-based solvents such as chloroform and methylene chloride, aromatic-based solvents such as benzene and toluene, ester-based solvents such as ethyl acetate, butyl acetate, and isopropyl acetate, ether-based solvents such as diethyl ether, tetrahydrofuran, and dioxane, and glycol ether-based solvents such as ethylene glycol monomethyl ether and ethylene glycol dimethyl ether.
- ketone-based solvents such as acetone, methyl ethyl ketone, and diethyl ketone
- alcohol-based solvents such as methanol
- the amount thereof added is in a range that does not cause problems with the solvent resistance or the VOC, and the amount is preferably in the range of 0.1 to 5 wt % relative to the total amount of the ink composition, and more preferably 0.1 to 3 wt %.
- the ink composition may contain various types of high molecular weight compounds in order to adjust film physical properties.
- the high molecular weight compounds include acrylic polymers, polyvinylbutyral resins, polyurethane resins, polyamide resins, polyester resins, epoxy resins, phenol resins, polycarbonate resins, polyvinylbutyral resins, polyvinylformal resins, shellac, vinylic resins, acrylic resins, rubber-based resins, waxes, and other natural resins. They may be used in a combination of two or more types. Among these, a vinylic copolymer obtained by copolymerization of an acrylic monomer is preferable.
- a copolymer component of the high molecular weight compound a copolymer containing as a structural unit a 'carboxyl group-containing monomer', an 'alkyl methacrylate ester', or an 'alkyl acrylate ester' may preferably be used.
- the basic compound is preferably added from the viewpoint of improving the storage stability of the ink composition.
- a basic compound that can be used in the present invention is a known basic compound, and preferred examples thereof include a basic inorganic compound such as an inorganic salt or a basic organic compound such as an amine.
- the composition may contain as necessary, for example, a leveling additive, a matting agent, a wax for adjusting film physical properties, or a tackifier in order to improve the adhesion to a recording medium such as polyolefin or PET, the tackifier not inhibiting polymerization.
- a leveling additive for example, a matting agent, a wax for adjusting film physical properties, or a tackifier in order to improve the adhesion to a recording medium such as polyolefin or PET, the tackifier not inhibiting polymerization.
- the tackifier include high molecular weight tacky polymers described on pp. 5 and 6 of JP-A-2001-49200 (e.g. a copolymer formed from an ester of (meth)acrylic acid and an alcohol having an alkyl group with 1 to 20 carbons, an ester of (meth)acrylic acid and an alicyclic alcohol having 3 to 14 carbons, or an ester of (meth)acrylic acid and an aromatic alcohol having 6 to 14 carbons), and a low molecular weight tackifying resin having a polymerizable unsaturated bond.
- high molecular weight tacky polymers described on pp. 5 and 6 of JP-A-2001-49200 e.g. a copolymer formed from an ester of (meth)acrylic acid and an alcohol having an alkyl group with 1 to 20 carbons, an ester of (meth)acrylic acid and an alicyclic alcohol having 3 to 14 carbons, or an ester of (meth)acrylic acid and an
- the ink composition has a viscosity at 25°C of preferably no more than 40 mPa ⁇ s, more preferably 5 to 40 mPa ⁇ s, and yet more preferably 7 to 30 mPa ⁇ s.
- the viscosity of the ink composition at the discharge temperature is preferably 3 to 15 mPa ⁇ s, and more preferably 3 to 13 mPa ⁇ s.
- it is preferable that its component ratio is appropriately adjusted so that the viscosity is in the above-mentioned range.
- the viscosity at room temperature is set to be high, even when a porous recording medium is used, penetration of the ink into the recording medium can be prevented, and uncured monomer can be reduced. Furthermore, ink spreading when ink droplets have landed can be suppressed, and as a result there is the advantage that the image quality is improved.
- the surface tension of the ink composition of the present invention at 25°C is preferably 20 to 35 mN/m, and more preferably 23 to 33 mN/m.
- recording medium such as polyolefin, PET, coated paper, and uncoated paper, from the viewpoint of spread and penetration, it is preferably at least 20 mN/m, and from the viewpoint of wettability it is preferably not more than 35 mN/m.
- the ink composition of the present invention is used for inkjet recording.
- the inkjet recording method of the present invention is a method for forming an image by discharging the ink composition of the present invention onto a recording medium (support, recording material, etc.) for inkjet recording and curing the ink by irradiating the ink composition so discharged onto the recording medium with actinic radiation.
- the inkjet recording method of the present invention comprises (a 1 ) a step of discharging the ink composition of the present invention onto a recording medium and (b 1 ) a step of curing the ink composition by irradiating the ink composition so discharged with actinic radiation,
- the inkjet recording method of the present invention comprises the steps (a 1 ) and (b 1 ) above and thus forms an image from the ink composition cured on the recording medium.
- the printed material of the present invention is a printed material recorded by the inkjet recording method of the present invention.
- the step (a 1 ) of the inkjet recording method of the present invention may employ an inkjet recording device that will be described in detail below.
- An inkjet recording device used in the inkjet recording method of the present invention is not particularly limited, and any known inkjet recording device that can achieve an intended resolution may be used. That is, any known inkjet recording device, such as a commercial product, may be used in order to discharge an ink onto a recording medium in step (a 1 ) of the inkjet recording method of the present invention.
- the inkjet recording device that can be used in the present invention is equipped with, for example, an ink supply system, a temperature sensor, and an actinic radiation source.
- the ink supply comprises, for example, a main tank containing the ink composition of the present invention, a supply pipe, an ink supply tank immediately before an inkjet head, a filter, and a piezo system inkjet head.
- the piezo system inkjet head may be driven so as to discharge a multisize dot of preferably 1 to 100 pL, and more preferably 8 to 30 pL, at a resolution of preferably 320 x 320 to 4,000 x 4,000dpi, more preferably 400 x 400 to 1,600 x 1,600dpi, and yet more preferably 720 x 720 dpi.
- dpi referred to in the present invention means the number of dots per 2.54 cm.
- a section from the ink supply tank to the inkjet head is thermally insulated and heated.
- a method of controlling temperature is not particularly limited, but it is preferable to provide, for example, temperature sensors at a plurality of pipe section positions, and control heating according to the ink flow rate and the temperature of the surroundings.
- the temperature sensors may be provided on the ink supply tank and in the vicinity of the inkjet head nozzle.
- the head unit that is to be heated is preferably thermally shielded or insulated so that the device main body is not influenced by the temperature of the outside air. In order to reduce the printer start-up time required for heating, or in order to reduce the thermal energy loss, it is preferable to thermally insulate the head unit from other sections and also to reduce the heat capacity of the entire heated unit.
- the ink composition is preferably discharged after being heated to preferably 25°C to 80°C, and more preferably 25°C to 50°C, so as to reduce the viscosity of the ink composition to preferably 3 to 15 mPa ⁇ s, and more preferably 3 to 13 mPa ⁇ s.
- the radiation curing type ink composition such as the ink composition of the present invention generally has a viscosity that is higher than that of a normal ink composition or a water-based ink used for an inkjet recording ink, and variation in viscosity due to a change in temperature at the time of discharge is large. Viscosity variation in the ink has a large effect on changes in liquid droplet size and changes in liquid droplet discharge speed and, consequently, causes the image quality to be degraded. It is therefore necessary to maintain the ink discharge temperature as constant as possible.
- the control range for the temperature is preferably ⁇ 5°C of a set temperature, more preferably ⁇ 2°C of the set temperature, and yet more preferably ⁇ 1°C of the set temperature.
- step (b 1 ) of curing the discharged ink composition by irradiating the ink composition with actinic radiation is now explained.
- the ink composition discharged onto the recording medium cures upon exposure to actinic radiation.
- an initiating species such as a radical, an acid, or a base being generated by decomposition of the polymerization initiator contained in the ink composition of the present invention by irradiation with actinic radiation, the initiating species functioning so as to make a polymerization reaction of a radically polymerizable compound take place and to promote it.
- the sensitizing colorant in the system absorbs actinic radiation, becomes excited, and promotes decomposition of the polymerization initiator by contact with the polymerization initiator, thus enabling a curing reaction with higher sensitivity to be achieved.
- the actinic radiation used in this process may include ⁇ rays, ⁇ rays, an electron beam, X rays, UV rays, visible light, and IR rays. Although it depends on the absorption characteristics of the sensitizing dye, the peak wavelength of the actinic radiation is, for example, 200 to 600 nm, preferably 300 to 450 nm, and more preferably 350 to 420 nm.
- the polymerization initiation system has sufficient sensitivity for low output actinic radiation.
- the actinic radiation is applied therefore so that the illumination intensity on the exposed surface is, for example, 10 to 4,000 mW/cm 2 , and preferably 20 to 2,500 mW/cm 2 .
- UV photocuring inkjet As an actinic radiation source, a mercury lamp, a gas/solid laser, etc. are mainly used, and for UV photocuring inkjet a mercury lamp and a metal halide lamp are widely known.
- a mercury lamp and a metal halide lamp are widely known.
- LEDs (UV-LED) and LDs (UV-LD) have small dimensions, long life, high efficiency, and low cost, and their use as a photocuring inkjet light source can be expected.
- light-emitting diodes and laser diodes (LD) may be used as the source of actinic radiation.
- a UV ray source when a UV ray source is needed, a UV-LED or a UV-LD may be used.
- Nichia Corporation has marketed a violet LED having a wavelength of the main emission spectrum of between 365 nm and 420 nm.
- US Pat. No. 6,084,250 discloses an LED that can emit actinic radiation whose wavelength is centered between 300 nm and 370 nm.
- another violet LED is available, and irradiation can be carried out with radiation of a different UV bandwidth.
- the actinic radiation source particularly preferable in the present invention is a UV-LED, and a UV-LED having a peak wavelength at 350 to 420 nm is particularly preferable.
- the maximum illumination intensity of the LED on a recording medium is preferably 10 to 2,000 mW/cm 2 , more preferably 20 to 1,000 mW/cm 2 , and particularly preferably 50 to 800 mJ/cm 2 .
- the ink composition of the present invention is desirably exposed to such actinic radiation for, for example, 0.01 to 120 sec., and preferably 0.1 to 90 sec.
- Irradiation conditions and a basic method for irradiation with actinic radiation are disclosed in JP-A-60-132767 .
- a light source is provided on either side of a head unit that includes an ink discharge device, and the head unit and the light source are made to scan by a so-called shuttle system.
- Irradiation with actinic radiation is carried out after a certain time (e.g. 0.01 to 0.5 sec., preferably 0.01 to 0.3 sec., and more preferably 0.01 to 0.15 sec.) has elapsed from when the ink has landed.
- WO99/54415 discloses, as an irradiation method, a method employing an optical fiber and a method in which a collimated light source is incident on a mirror surface provided on a head unit side face, and a recorded area is irradiated with UV light.
- the ink composition of the present invention is cured by irradiation with actinic radiation in high sensitivity to thus form an image on the surface of the recording medium.
- the inkjet recording method of the present invention may suitably employ the ink set of the present invention.
- the order in which colored ink compositions are discharged is not particularly limited, but it is preferable to apply to a recording medium from a colored ink composition having a low lightness; when the ink composition of the present invention and yellow, cyan, magenta, and black are used, they are preferably applied on top of the recording medium in the order ink composition(s) of the present invention ⁇ yellow ⁇ cyan ⁇ magenta ⁇ black. Furthermore, when white is additionally used, they are preferably applied on top of the recording medium in the order white ⁇ ink composition(s) of the present invention ⁇ yellow ⁇ cyan ⁇ magenta ⁇ black.
- an ink set of the present invention comprising a total of eight colors, that is, light cyan, light magenta, and light black ink compositions of the present invention and cyan, magenta, black, white, and yellow dark ink compositions may preferably be used, and in this case they are applied on top of the recording medium in the order white ⁇ light cyan ⁇ light magenta ⁇ light black ⁇ yellow ⁇ cyan ⁇ magenta ⁇ black.
- the recording medium is not particularly limited, and a recording medium known as a support or a recording material may be used.
- a recording medium known as a support or a recording material examples thereof include paper, paper laminated with a plastic (e.g. polyethylene, polypropylene, polystyrene, etc.), a metal plate (e.g. aluminum, zinc, copper, etc.), a plastic film (e.g. cellulose diacetate, cellulose triacetate, cellulose propionate, cellulose butyrate, cellulose acetate butyrate, cellulose nitrate, polyethylene terephthalate, polyethylene, polystyrene, polypropylene, polycarbonate, polyvinylacetal, etc.), and paper or plastic film laminated or vapor-deposited with the above metal.
- a non-absorbing recording medium may suitably be used as the recording medium.
- the ink set of the present invention is not particularly limited as long as it is an ink set having two or more types of ink compositions in combination, the ink set comprising in combination at least one ink composition of the present invention and another ink composition of the present invention or an ink composition other than one of the present invention, and it is preferable for the ink set to comprise at least one ink composition of the present invention having a color selected from light magenta, light cyan, and light black (gray).
- the ink set of the present invention may be suitably used in the inkjet recording method of the present invention.
- an ink set of the present invention an ink set comprising in combination four dark ink compositions of yellow, cyan, magenta, and black and at least one ink composition of the present invention
- the 'dark ink composition' referred to in the present invention means an ink composition for which the content of the colorant exceeds 1 wt % of the entire ink composition.
- the colorant is not particularly limited; a known colorant may be used, and examples thereof include a pigment and an oil-soluble dye.
- the ink set of the present invention may comprise an ink composition containing a colorant other than a pigment at 1 wt % or less.
- the ratio is in the above-mentioned range, a vivid full color image with little feeling of grain can be obtained.
- compositions used in the present invention are as follows.
- IRGALITE BLUE GLVO cyan pigment, manufactured by Ciba Specialty Chemicals
- CINQUASIA MAGENTA RT-335 D magenta pigment, manufactured by Ciba Specialty Chemicals
- NOVOPERM YELLOW H2G yellow pigment, manufactured by Clariant
- SPECIAL BLACK 250 black pigment, manufactured by Ciba Specialty Chemicals
- Tipaque CR60-2 white pigment, manufactured by Ishihara Sangyo Kaisha Ltd.
- Solsperse 32000 (manufactured by Noveon)
- Solsperse 36000 (manufactured by Noveon)
- Solsperse 22000 (manufactured by Noveon)
- OXT-221 manufactured by Toagosei Co., Ltd.
- OXT-211 manufactured by Toagosei Co., Ltd.
- OXT-212 manufactured by Toagosei Co., Ltd.
- CPI-100P (sulfonium salt, manufactured by San-Apro Ltd.)
- Dibutoxyanthracene (manufactured by Kawasaki Kasei Chemicals Ltd.)
- Mill bases for radically polymerizable compositions were prepared as follows.
- cyan mill base A 300 parts by weight of IRGALITE BLUE GLVO, 600 parts by weight of Actilane 421, and 100 parts by weight of Solsperse 32000 were stirred and mixed to give cyan mill base A.
- Preparation of cyan mill base A was carried out by putting it into an M50 disperser motor mill (manufactured by Eiger) and dispersing using zirconia beads having a diameter of 0.65 mm at a peripheral speed of 9 m/s for 4 hours.
- magenta mill base B 300 parts by weight of CINQUASIA MAGENTA RT-335 D, 600 parts by weight of Actilane 421, and 100 parts by weight of Solsperse 32000 were stirred and mixed to give magenta mill base B.
- Preparation of magenta mill base B was carried out by putting it into an M50 disperser motor mill (manufactured by Eiger) and dispersing using zirconia beads having a diameter of 0.65 mm at a peripheral speed of 9 m/s for 10 hours.
- black mill base D 300 parts by weight of SPECIAL BLACK 250, 600 parts by weight of Actilane 421, and 100 parts by weight of Solsperse 32000 were stirred and mixed to give black mill base D.
- Preparation of black mill base D was carried out by putting it into an M50 disperser motor mill (manufactured by Eiger) and dispersing using zirconia beads having a diameter of 0.65 mm at a peripheral speed of 9 m/s for 7 hours.
- white mill base E 500 parts by weight of Tipaque CR60-2, 450 parts by weight of NK ESTER AMP-10G, and 50 parts by weight of Solsperse 36000 were stirred and mixed to give white mill base E.
- Preparation of white mill base E was carried out by putting it into an M50 disperser motor mill (manufactured by Eiger) and dispersing using zirconia beads having a diameter of 0.65 mm at a peripheral speed of 9 m/s for 4 hours.
- cyan mill base F 300 parts by weight of IRGALITE BLUE GLVO, 500 parts by weight of Actilane 421, and 200 parts by weight of Disper BYK-168 were stirred and mixed to give cyan mill base F.
- Preparation of cyan mill base F was carried out by putting it into an M50 disperser motor mill (manufactured by Eiger) and dispersing using zirconia beads having a diameter of 0.65 mm at a peripheral speed of 9 m/s for 4 hours.
- magenta mill base G 300 parts by weight of CINQUASIA MAGENTA RT-335 D, 400 parts by weight of Actilane 421, and 300 parts by weight of Disper BYK-168 were stirred and mixed to give magenta mill base G.
- Preparation of magenta mill base G was carried out by putting it into an M50 disperser motor mill (manufactured by Eiger) and dispersing using zirconia beads having a diameter of 0.65 mm at a peripheral speed of 9 m/s for 10 hours.
- black mill base H 300 parts by weight of SPECIAL BLACK 250, 500 parts by weight of Actilane 421, and 200 parts by weight of Disper BYK-168 were stirred and mixed to give black mill base H.
- Preparation of black mill base H was carried out by putting it into an M50 disperser motor mill (manufactured by Eiger) and dispersing using zirconia beads having a diameter of 0.65 mm at a peripheral speed of 9 m/s for 7 hours.
- cyan mill base I 300 parts by weight of IRGALITE BLUE GLVO, 600 parts by weight of Actilane 421, and 100 parts by weight of Solsperse 22000 were stirred and mixed to give cyan mill base I.
- Preparation of cyan mill base I was carried out by putting it into an M50 disperser motor mill (manufactured by Eiger) and dispersing using zirconia beads having a diameter of 0.65 mm at a peripheral speed of 9 m/s for 4 hours.
- Mill bases for cationically polymerizable compositions were prepared as follows.
- cyan mill base J 300 parts by weight of IRGALITE BLUE GLVO, 600 parts by weight of OXT-212, and 100 parts by weight of Solsperse 32000 were stirred and mixed to give cyan mill base J.
- Preparation of cyan mill base J was carried out by putting it into an M50 disperser motor mill (manufactured by Eiger) and dispersing using zirconia beads having a diameter of 0.65 mm at a peripheral speed of 9 m/s for 3 hours.
- magenta mill base K 300 parts by weight of CINQUASIA MAGENTA RT-335 D, 600 parts by weight of OXT-212, and 100 parts by weight of Solsperse 32000 were stirred and mixed to give magenta mill base K.
- Preparation of magenta mill base K was carried out by putting it into an M50 disperser motor mill (manufactured by Eiger) and dispersing using zirconia beads having a diameter of 0.65 mm at a peripheral speed of 9 m/s for 8 hours.
- yellow mill base L 300 parts by weight of NOVOPERM YELLOW H2G, 600 parts by weight of OXT-212, and 100 parts by weight of Solsperse 32000 were stirred and mixed to give yellow mill base L.
- Preparation of yellow mill base L was carried out by putting it into an M50 disperser motor mill (manufactured by Eiger) and dispersing using zirconia beads having a diameter of 0.65 mm at a peripheral speed of 9 m/s for 8 hours.
- black mill base M 300 parts by weight of SPECIAL BLACK 250, 600 parts by weight of OXT-212, and 100 parts by weight of Solsperse 32000 were stirred and mixed to give black mill base M.
- Preparation of black mill base M was carried out by putting it into an M50 disperser motor mill (manufactured by Eiger) and dispersing using zirconia beads having a diameter of 0.65 mm at a peripheral speed of 9 m/s for 5.5 hours.
- white mill base N 500 parts by weight of Tipaque CR60-2, 450 parts by weight of OXT-212, and 50 parts by weight of Solsperse 36000 were stirred and mixed to give white mill base N.
- Preparation of white mill base N was carried out by putting it into an M50 disperser motor mill (manufactured by Eiger) and dispersing using zirconia beads having a diameter of 0.65 mm at a peripheral speed of 9 m/s for 3 hours.
- cyan mill base O 300 parts by weight of IRGALITE BLUE GLVO, 500 parts by weight of OXT-212, and 200 parts by weight of Disper BYK-168 were stirred and mixed to give cyan mill base O.
- Preparation of cyan mill base O was carried out by putting it into an M50 disperser motor mill (manufactured by Eiger) and dispersing using zirconia beads having a diameter of 0.65 mm at a peripheral speed of 9 m/s for 3 hours.
- magenta mill base P 300 parts by weight of CINQUASIA MAGENTA RT-335 D, 400 parts by weight of OXT-212, and 300 parts by weight of Disper BYK-168 were stirred and mixed to give magenta mill base P.
- Preparation of magenta mill base P was carried out by putting it into an M50 disperser motor mill (manufactured by Eiger) and dispersing using zirconia beads having a diameter of 0.65 mm at a peripheral speed of 9 m/s for 8 hours.
- black mill base Q 300 parts by weight of SPECIAL BLACK 250, 500 parts by weight of OXT-212, and 200 parts by weight of Disper BYK-168 were stirred and mixed to give black mill base Q.
- Preparation of black mill base Q was carried out by putting it into an M50 disperser motor mill (manufactured by Eiger) and dispersing using zirconia beads having a diameter of 0.65 mm at a peripheral speed of 9 m/s for 5.5 hours.
- cyan mill base R 300 parts by weight of IRGALITE BLUE GLVO, 600 parts by weight of OXT-212, and 100 parts by weight of Solsperse 22000 were stirred and mixed to give cyan mill base R.
- Preparation of cyan mill base R was carried out by putting it into an M50 disperser motor mill (manufactured by Eiger) and dispersing using zirconia beads having a diameter of 0.65 mm at a peripheral speed of 9 m/s for 3 hours.
- the ink supply system comprised a main tank, a supply pipe, an ink supply tank immediately before an inkjet head, a filter, and a piezo type inkjet head, and a section from the ink supply tank to the inkjet head was thermally insulated and heated. Temperature sensors were provided on the ink supply tank and in the vicinity of the nozzle of the inkjet head, and the temperature was controlled so that the nozzle section was always at 45°C ⁇ 2°C.
- the piezo type inkjet head was driven so as to discharge multisize dots of 8 to 30 pL at a resolution of 720 x 720 dpi.
- the exposure system, the main scanning speed, and the discharge frequency were adjusted so that, after landing, UV light was focused to give an exposure area illumination intensity of 1,630 mW/cm 2 , and irradiation started 0.1 sec. after the ink landed on the recording medium.
- the cumulative amount of light applied to an image was adjusted so as to be 1,500 mJ/cm 2 .
- the UV lamp employed a HAN250NL high-cure mercury lamp (manufactured by GS Yuasa Corporation).
- dpi referred to in the present invention denotes the number of dots per 2.54 cm.
- the recording medium employed an E5000 ester film (film thickness 125 ⁇ m, manufactured by Toyobo Co., Ltd.).
- a solid printed image having an average film thickness of 12 ⁇ m was formed, and the stickiness of the image was evaluated by touch after the image was irradiated with ultraviolet rays.
- the curing sensitivity was evaluated using the following criteria.
- an E5000 ester film (film thickness 125 ⁇ m, manufactured by Toyobo Co., Ltd.) was used as a recording medium, and three solid printed images having average image area film thicknesses of 12 ⁇ m, 24 ⁇ m, and 36 ⁇ m were formed.
- the bending test involved bending once at 25°C the recording medium on which an image had been formed, and an evaluation was carried out of the presence or absence of cracks in the image area. In general, when the average film thickness was large, the distortion occurring in the image area when bending the image area became large, and cracks easily occurred. That is, testing whether or not cracks occurred in an image area having a larger film thickness gave a measure of the flexibility.
- the evaluation criteria were as follows.
- particle size was measured using an FPAR-1000 (manufactured by Otsuka Electronics Co., Ltd.).
- OXT-221 was used as a diluent solvent in order to adjust the concentration.
- the components below were stirred using a high-speed water-cooled stirrer to give a light black UV inkjet ink.
- the viscosity was 17 mPa ⁇ s.
- magenta mill base B 13.0 parts Disper BYK-168 2.0 parts
- FANCRYL 512A 55.4 parts
- N -Vinylcaprolactam 10.0 parts
- KAYARAD DPCA-60 1.4 parts
- Rapi-Cure DVE-3 3.0 parts
- FIRSTCURE ST-1 0.3 parts Lucirin TPO 9.0 parts Benzophenone 3.2 parts FIRSTCURE ITX 3.00 parts KF-353 0.06 parts
- the inkjet recording device had a total of eight ink supply systems, and each ink supply system independently comprised a main tank, a supply pipe, an ink supply tank immediately before an inkjet head, a filter, and a piezo type inkjet head.
- the ink tanks were charged respectively with the light cyan ink, the light magenta ink, and the light black ink prepared in Examples 1 to 3, and the cyan ink R1, the magenta ink R2, the yellow ink R3, the black ink R4, and the white ink R5, and a section from the ink supply tank to the inkjet head was thermally insulated and heated.
- Temperature sensors were provided on the ink supply tank and in the vicinity of the nozzle of the inkjet head, and the temperature was controlled so that the nozzle section was always at 45°C ⁇ 2°C.
- Eight of the piezo type inkjet heads were arranged in parallel and were driven simultaneously so as to discharge multisize dots of 8 to 30 pL at a resolution of 720 x 720 dpi.
- the exposure system, the main scanning speed, and the discharge frequency were adjusted so that, after landing, UV light was focused to give an exposure area illumination intensity of 1,630 mW/cm 2 , and irradiation started 0.1 to 0.3 sec. after the ink landed on the recording medium.
- the cumulative amount of light applied to an image was adjusted so as to be 1,500 mJ/cm 2 .
- the UV lamp employed an HAN250NL high-cure mercury lamp (manufactured by GS Yuasa Corporation).
- dpi referred to in the present invention denotes the number of dots per 2.54 cm.
- the recording medium employed an E5000 ester film (film thickness 125 ⁇ m, manufactured by Toyobo Co., Ltd.).
- a 12 ⁇ m thick composite black solid image was formed using all 8 of the inks charged. The results are given in Table 1.
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- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- Ink Jet Recording Methods And Recording Media Thereof (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
- Ink Jet (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
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JP2007044894A JP5227521B2 (ja) | 2007-02-26 | 2007-02-26 | インク組成物、インクジェット記録方法、印刷物、及び、インクセット |
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EP1964893A1 true EP1964893A1 (fr) | 2008-09-03 |
EP1964893B1 EP1964893B1 (fr) | 2018-01-24 |
EP1964893B2 EP1964893B2 (fr) | 2021-11-24 |
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EP08002529.9A Active EP1964893B2 (fr) | 2007-02-26 | 2008-02-12 | Composition d'encre, procédé d'enregistrement à jet d'encre, matériau imprimé et ensemble d'encres |
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US (1) | US20080206527A1 (fr) |
EP (1) | EP1964893B2 (fr) |
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JPS4537377B1 (fr) | 1965-06-03 | 1970-11-27 | ||
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JPS4842965B1 (fr) | 1968-04-02 | 1973-12-15 | ||
JPS476416B1 (fr) | 1968-04-16 | 1972-02-23 | ||
JPS473981B1 (fr) | 1968-06-11 | 1972-02-03 | ||
JPS4722326B1 (fr) | 1968-07-26 | 1972-06-22 | ||
JPS4723664B1 (fr) | 1968-07-26 | 1972-07-01 | ||
JPS4642363B1 (fr) | 1968-10-09 | 1971-12-15 | ||
JPS4830492B1 (fr) | 1969-10-07 | 1973-09-20 | ||
GB1388492A (en) | 1971-09-03 | 1975-03-26 | Minnesota Mining & Mfg | Chromophore-substituted halomethyl-s-triazines |
JPS5534414B2 (fr) | 1972-06-02 | 1980-09-06 | ||
JPS6026483B2 (ja) | 1972-07-28 | 1985-06-24 | チバ・ガイギ−・アクチエンゲゼルシヤフト | 不飽和化合物を含む重合系の光重合反応用増感剤 |
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JPS5214279B2 (fr) | 1974-05-02 | 1977-04-20 | ||
JPS5214278B2 (fr) | 1974-05-02 | 1977-04-20 | ||
JPS5182102A (en) | 1974-12-10 | 1976-07-19 | Basf Ag | Insatsuinki oyobi hifukuzairyonotameno hikarijugokanonaketsugozai |
JPS5621141B2 (fr) | 1975-10-16 | 1981-05-18 | ||
JPS53702A (en) | 1975-12-23 | 1978-01-06 | Dynachem Corp | Adhesion promoting agent for polymerized film |
JPS52134692A (en) | 1976-05-04 | 1977-11-11 | Fuji Photo Film Co Ltd | Photopolymerizable composition |
DE2641100A1 (de) | 1976-09-13 | 1978-03-16 | Hoechst Ag | Lichtempfindliche kopierschicht |
JPS53133022A (en) | 1977-04-23 | 1978-11-20 | Du Pont | Light sensitive element |
JPS53133428A (en) | 1977-04-25 | 1978-11-21 | Hoechst Ag | Radiation sensitive copying constitute |
JPS6026403B2 (ja) | 1977-05-17 | 1985-06-24 | メルク・パテント・ゲゼルシヤフト・ミツト・ベシユレンクテル・ハフツング | 不飽和化合物の光重合用光増感剤 |
JPS5448535A (en) | 1977-08-31 | 1979-04-17 | Konishiroku Photo Ind Co Ltd | Color photographic material |
JPH0134242B2 (fr) | 1977-12-22 | 1989-07-18 | Ciba Geigy | |
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JPS579053B2 (fr) | 1978-01-09 | 1982-02-19 | ||
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JPS6340799B2 (fr) | 1978-07-14 | 1988-08-12 | Basf Ag | |
JPS608047B2 (ja) | 1978-07-14 | 1985-02-28 | バスフ アクチェン ゲゼルシャフト | 光硬化性のポリエステル樹脂組成物 |
JPS55500806A (fr) | 1978-10-19 | 1980-10-16 | ||
JPS626223B2 (fr) | 1979-03-06 | 1987-02-09 | Fuji Photo Film Co Ltd | |
JPS5942864B2 (ja) | 1979-04-13 | 1984-10-18 | 京セラミタ株式会社 | 投影用原稿の作成方法及びそれに用いる静電写真用転写フイルム |
JPS5675643A (en) | 1979-11-07 | 1981-06-22 | Hoechst Ag | Photopolymerizable mixture and photopolymerizable copying material using same |
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JPH029596B2 (fr) | 1980-05-27 | 1990-03-02 | Basf Ag | |
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JPS5730704A (en) | 1980-06-24 | 1982-02-19 | Bayer Ag | Photopolymerizable mixture containing aroylphosphoric acid ester as photoinitiator |
EP0044115A1 (fr) | 1980-07-14 | 1982-01-20 | Akzo N.V. | Composition de revêtement thermodurcissable contenant un catalyseur acide bloqué |
EP0046083A2 (fr) | 1980-08-11 | 1982-02-17 | Minnesota Mining And Manufacturing Company | Agents surfactifs bloqués photolabiles et compositions de revêtement les contenant |
JPH029597B2 (fr) | 1980-09-15 | 1990-03-02 | Basf Ag | |
JPS6314340B2 (fr) | 1980-09-17 | 1988-03-30 | Fuji Photo Film Co Ltd | |
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JPS6361950B2 (fr) | 1981-03-16 | 1988-11-30 | ||
JPS57156264A (en) | 1981-03-20 | 1982-09-27 | Fuji Photo Film Co Ltd | Ink jet recording system |
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EP0084515A2 (fr) | 1982-01-11 | 1983-07-27 | Ciba-Geigy Ag | Composition durcissable par un acide contenant un catalyseur masqué et procédé de durcissement |
JPS58185677A (ja) | 1982-04-22 | 1983-10-29 | Konishiroku Photo Ind Co Ltd | 紫外線吸収剤 |
EP0101122A1 (fr) | 1982-08-09 | 1984-02-22 | Akzo N.V. | Composition de revêtement thermodurcissable contenant un acide bloqué comme catalyseur |
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JPS59138205A (ja) | 1983-01-20 | 1984-08-08 | チバ−ガイギ− アクチエンゲゼルシヤフト | 被覆組成物およびその硬化方法 |
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JPS59174831A (ja) | 1983-03-24 | 1984-10-03 | Fuji Photo Film Co Ltd | 光重合性組成物 |
JPS6084305A (ja) | 1983-08-30 | 1985-05-13 | バスフ アクチェン ゲゼルシャフト | 光重合可能な混合物 |
JPS6056557A (ja) | 1983-09-09 | 1985-04-02 | Canon Inc | インクジェット記録方法 |
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JPS60132767A (ja) | 1983-12-21 | 1985-07-15 | Seikosha Co Ltd | インクジエツトプリンタ |
EP0156153A1 (fr) | 1984-03-22 | 1985-10-02 | Maschinenfabrik Rieter Ag | Dispositif pour contrôler la qualité du fil |
JPS60198538A (ja) | 1984-03-22 | 1985-10-08 | Toshiba Corp | ポジ型レジスト材料 |
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JPS61151197A (ja) | 1984-12-20 | 1986-07-09 | チバ‐ガイギー アーゲー | チタノセン類およびこれらのチタノセン類を含有する照射重合開始剤 |
JPS61190537A (ja) | 1985-01-22 | 1986-08-25 | チバーガイギー アクチエンゲゼルシヤフト | 2―(2―ヒドロキシ―3―分枝アルキル―5―メチルフェニル)―2h―ベンゾトリアゾール混合物,該混合物の製造法,および該混合物からなる安定剤 |
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JPS6221572A (ja) | 1985-07-22 | 1987-01-29 | Canon Inc | 記録装置 |
JPS6258241A (ja) | 1985-09-09 | 1987-03-13 | Fuji Photo Film Co Ltd | 感光性組成物 |
JPS6281345A (ja) | 1985-09-28 | 1987-04-14 | チバ―ガイギー アクチェンゲゼルシャフト | 共重合性光開始剤 |
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JPS62135826A (ja) | 1985-12-09 | 1987-06-18 | Konishiroku Photo Ind Co Ltd | 熱現像感光材料 |
JPS62173463A (ja) | 1986-01-28 | 1987-07-30 | Fuji Photo Film Co Ltd | 画像形成方法 |
JPS62183457A (ja) | 1986-02-07 | 1987-08-11 | Fuji Photo Film Co Ltd | 画像形成方法 |
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JPS62262047A (ja) | 1986-04-30 | 1987-11-14 | イ−ストマン コダツク カンパニ− | 写真要素 |
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Cited By (6)
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EP2169021A1 (fr) * | 2008-09-25 | 2010-03-31 | Fujifilm Corporation | Composition d'encre, procédé d'enregistrement à jet d'encre, et matériau imprimé |
EP2230284A1 (fr) * | 2009-03-17 | 2010-09-22 | Fujifilm Corporation | Tintenzusammensetzung und Tintenaufzeichnungsverfahren |
EP2471879A1 (fr) * | 2010-12-28 | 2012-07-04 | Fujifilm Corporation | Jeu d'encre pour enregistrement à jet d'encre, procédé d'enregistrement à jet d'encre et matériau imprimé |
CN102585599A (zh) * | 2010-12-28 | 2012-07-18 | 富士胶片株式会社 | 喷墨记录用油墨组、喷墨记录方法及印刷物 |
EP2707442A4 (fr) * | 2011-05-12 | 2015-08-26 | Ricoh Co Ltd | Encre à jet d'encre photopolymérisable, cartouche d'encre et dispositif d'enregistrement à jet d'encre |
US9428665B2 (en) | 2011-05-12 | 2016-08-30 | Ricoh Company, Ltd. | Photopolymerizable inkjet ink, ink cartridge, and inkjet recording device |
Also Published As
Publication number | Publication date |
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EP1964893B2 (fr) | 2021-11-24 |
US20080206527A1 (en) | 2008-08-28 |
JP2008208190A (ja) | 2008-09-11 |
EP1964893B1 (fr) | 2018-01-24 |
JP5227521B2 (ja) | 2013-07-03 |
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